The Best Men’s Socks

If you’ve downloaded any of my Free Ebooks, then you already know I’ve got some pretty strong opinions about socks – especially white ones. Most of my clients come to me with a drawer full of white, mid-calf length socks, possibly some ankle socks thrown in there, and a ratty pair or two of dress socks they pull out from time to time. This is unacceptable and frankly… gross. Before I took my nephew George under my wing, his sock drawer looked like this, but he had an excuse – he’s a little kid!

Socks area one of the few items in menswear when it’s perfectly acceptable to go absolutely crazy without looking ridiculous. You can use them to show off some of your personality and have fun with them. I’ve got clients who wear their favorite sports teams, crazy patterns, super heroes, etc. People will only really see them when you’re seated and they’re great conversation pieces, so I say go bonkers with them!

The Cardinal Sin of Socks

The only rule you cannot break from this day forward is: NO WHITE SOCKS – EVER. That’s it. They’re the cancer of the sock world. There’s no excuse or reason for owning any white socks anymore.

How many Socks Should I Own?

How many plain & patterned dress socks to have depends on what you wear and how often. I would say have enough to get you through a week, so about 7 pairs.

Best Material For Socks

Socks come in all sorts of fabrics/materials – wool, cotton, cashmere, silk, nylon or blends of each. In my experience, merino wool and cotton blends are best, because they’re more forgiving and comfortable than the other fabrics. They also look great and can be worn with both casual and dress outfits, and they’re just the right thickness. My choices at the bottom of this page will come in either fabric or one or the other. Silk, silk-blended or nylon-blended socks can only be worn with suits and dress shoes and will wear out quicker than other fabrics.

The types of socks to own

Plain & Patterned Dress Socks

I say dress socks, which are usually thinner than regular white socks, but I really just mean colored socks of any material. Think of these as your replacements for your white socks.

Like I said, it’s perfectly acceptable to go crazy here, but you should also at least have the standard colors of Black, Gray/Charcoal, and Navy in your sock drawer. That way, if you’re going to something where maybe it’s not appropriate – like a funeral or when it’s best to be more conservative.

As for material, like I said in the materials section, stick with merino wool or cotton blends because they’re most comfortable and can be worn with casual and dressy outfits. Just beware: Thick cotton or wool socks looks horrible with suits because they’re just too thick and informal. So if you need socks like that, wear them with casual outfits only.

Ankle Socks

These are to be worn when working out ONLY.

These are sometimes called low or short socks, depending on the company. Either way, they should have a little lip at the top. Anything higher, is to be avoided.

As for color, stick with black. White or other colors will get dirty and look gross very quickly.

For materials, merino wool or cotton blends are best.

No show socks

These are appropriate for when you’re wearing shorts or cuffing your pants with any type of shoes – loafers, boat shoes, dress shoes, sneakers, etc.

You want to go with black because it’ll look the best the longest. You can also go with patterns and other colors, but no one will really see it, so it’s a bit of a waste. If you’re wearing white shoes, you can wear white ones, but they tend to get gross and nasty pretty quickly so I just avoid them. Whatever you do, don’t get nude-colored ones. It’s really gross looking.

How to match socks to an outfit

Patterned Or Colored Socks

(Any colors or patterns outside of the standard colors I listed above – black, charcoal & navy.)

The best thing to do, and what I do with my clients, is have a color in the socks, regardless of whether they’re plain or patterned, that is similar to a shade of any item in an outfit – whether it be your shoes, pants, shirts or accessories.

So if your tie or pocket square has a bit of blue in it, wear some socks with blue in them.

Just don’t match your socks to your shirt color if it’s white. Again – NO WHITE SOCKS!

Standard Plain Colored Socks

(Black, Charcoal & Navy)

Jeans and any color sneakers = any of the 3 standard colors.

Black suit (you better be wearing black shoes only!) = black socks

Navy suit (shoe color doesn’t matter) = navy or charcoal socks

Gray suit w/ black shoes = charcoal or black socks

Gray suit w/ brown shoes = charcoal socks

With that said, though, you shouldn’t worry about matching 99% of the time, though, because socks are one of the few places in menswear when you can (and should) go absolutely bananas.

When should you replace your socks?

When they’re worn thin in certain areas – usually around the heel or toes.

When they’re faded, stretched out or stained.

When they’re severely pilled (those weird little balls of fabric usually around worn areas are called pills). Pilling is usually the beginnings of them starting to get worn out in that area.

The Best Men’s Socks

Plain & Patterned Dress Socks

Darn Tough

They’re some of my client’s favorites – and mine, of course. They’re soft, super comfortable and about as durable as any socks I’ve encountered.

The kicker is that they come with a lifetime warranty, so if anything happens to them, send the company an email and they’ll replace them free of charge, for life. Obviously, this comes at a price, because they’re not cheap, but I don’t find the price too offensive compared to other brands that don’t offer a lifetime guarantee.

They’re a merino blend, so they wick sweat and moisture away from your feet, keep them cool in the summer and warm in the winter. They’re also seamless on the toes, so you’ll never have to deal with the discomfort of excess fabric around your toes.

Their cushion versions are the best, but even their non-cushioned socked are great. I found the other sizes, like their micro crew, to be too short and you’ll be flashing some shin when crossing your legs – which is to be avoided – so stick to the crew length or mid-calf lengths.

The only annoying thing is that they don’t sell socks directly, so you have to get them via third parties, like Amazon, REI or GearX

Uniqlo

If you want a great budget-friendly cotton options with LOTS of different colors and patterns, look no further than Uniqlo’s Crew Socks.

Kirkland & Gold Toe

These are good for plain/traditional colored socks. Unless you’re a member of Costco, you won’t be able to get the Kirkland Signature Cushioned socks.

Gold Toe’s are the old standby and are great for their price, but you’ll be replacing them once ever six to 12 months.

Ankle Socks

Just like with their dress socks, I really love Darn Tough Ankle Socks. They’re comfortable as hell and come with that amazing lifetime guarantee.

For budget-friendly and variety, almost nowhere beats Uniqlo. They call their ankle socks “short” socks.

No Show Socks

I honestly say get the cheapest ones you can find because they’re all very similar. Some companies sell cotton blends and others sell more thin, nylon blended socks.

Some clients prefer one type over another, some like to have both and wear the thinner ones with dress shoes and the thicker ones with sneakers. This one is up to you, so try both and see what you prefer!

Again, Uniqlo reigns supreme! They call them “low cut” socks.

Dopp Kit or Toiletry Bag

If you ever travel, even if it’s just across town for the night, or to the gym, then you absolutely need a dopp kit or toiletry bag. No proper gentleman should ever be without one.

Why Own a dopp kit or Toiletry Bag?

The reasons you need one are many, but allow me to give a woman’s perspective and reasons for a moment.

In dating and life, we’re always looking at the smaller, subtle details to learn a little more about a person. We’re more sensitive to these subtleties and when a client asks why a dopp kit is important to own, I tell him that when a woman sees a man is organized and respects himself enough to have nice things, it makes us feel validated, like we found “a good one” because this small detail supports a notion that he probably has his life together and is a potentially good mate. It’s a very visceral, biological reaction that we get.

I often say it’s a similar thought to the old saying, “A messy bed equals a messy head” meaning that the way someone’s bed looks gives you some insight into their mental state.

On top of that, it’ll make traveling or going to the gym that much quicker and easier for you by keeping all your toiletries nice and organized. It’ll also help protect your clothing and luggage if you ever have any toiletries leak or spill.

What should a Dopp Kit do?

It should carry your toiletries, of course.
You also want it to be easy to use. There’s a lot of dopp kits out there, but my favorites are always the zip top style (see my choices below for examples) because the other styles aren’t as easy to pack or access items without having to move other things around. I had a client take a big chunk of out his finger with his razor while carelessly going through his non-top loading Dopp Kit and that’s what started me on the quest to find the perfect one. The next best alternative is the wide-mouth style (see the Shinola example below), but I find these tend to sacrifice some storage space to have the hinge. Even the original Dopp kit does this. My example below is the best I found with a hinge because it takes up less space than similar bags.
The last thing your Dopp Kit should do is last for the rest of your life. Unless things change dramatically over the course of your life, this should be the last one you ever buy. So if you’re hesitant because of pricing, don’t be. The cost per year will be so small that it’s absolutely worth it.

What Should it be made of?

Like with all the other bags I recommend in this series, I think there’s just no substitute for leather. It doesn’t stain as easily, and those stains will happen much quicker than your other items since it’s close to a lot of water and toothpaste, etc. Also, leather just looks much classier. Cloth or plastic alternatives are okay, but they just don’t compare, in my eyes.

What color should it be?

Just like all your other accessories, black or brown are my favorites. You can definitely go with other colors since not many people will see it, but I always stick to the classics here. Do you need to match it to your weekender bag? I would default to yes, because why not? But if you really like a brown dopp kitt and own a black weekender bag, then I don’t see an issue with that.

The Best Dopp Kits or Toiletry Bags

Jack Spade Leather Dopp Kit

Buy the Jack Leather Dopp Kit

It is my absolute favorite and one I’ve gifted to a lot of family and friends over the years. It’s simple, not too big or small, and has my favorite zip top design, so it’s very easy to access your items. I like just the simple pocket on the top, as well as the small side pockets for items that can fit there. Like all dopp kits should have, it of course has a waterproof lining, so if anything spills, it won’t be a total disaster for the items in your luggage.

I’d say that this one is perfect in every way.

Shinola Travel Kit

Shinola Dopp Travel Toiletries Kit Ashley Weston2

Shinola Dopp Travel Toiletries Kit Ashley Weston3

Buy the Shinola Travel Kit

This is one of the few traditional style dopp kits that I could find with a hinge top opening, which allows you to access the entire compartment. Shinola’s leather is really damn good and even though it only comes in black, if you prefer this shape over the zip top style, this one is definitely for you.

This Is Ground Tech Dopp Kit

ThisIsGroundTechDoppTravelToiletriesKit Ashley Weston1

ThisIsGroundTechDoppTravelToiletriesKit Ashley Weston3

ThisIsGroundTechDoppTravelToiletriesKit Ashley Weston4

ThisIsGroundTechDoppTravelToiletriesKit Ashley Weston5

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Buy a This Is Ground Tech Dopp Kit

While these are not technically a toiletry bag or dopp kit, they call it their “Tech Dopp Kit”, I’ve found the multiple size opens and construction as close to perfect as possible. The only thing it’s missing is the waterproof lining, but as long as you’re relatively careful with packing your liquids, it wouldn’t call this a deal breaker.

I show the different sizes in the video at the top of this page, but I would recommend you get their “regular” size since it’s comparable to your average dopp kit’s size. But if you want something smaller or bigger, I think it’s great that they have those options available, too.

Definitely get it monogramed for that little extra special touch!

KILLSPENCER Dopp/Folio 2.0

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KillSpencerdoppfolio_flat_black_2_3Ashley Weston

Buy the KILLSPENCER Dopp/Folio 2.0

Like all their products, it has a nice, supple leather with a great, tactical edge. I like it a lot because it has a unique look compared to all the other dopp kits out there and the inside is fully waterproof, so if anything spills, it won’t be a total disaster. While not a requirement, when you’re not using it as a dopp kit, it can also double as a folio by squishing it down a little bit. I thought this was a nice touch, but I don’t know how often it would be used like this. It’s definitely on the larger side of the spectrum, so if you’re looking for a larger dopp, this one is right for you.

Sunglasses

So we’ve already established (in the series intro video) that the details in your wardrobe & appearance matter, and just like I talked about before, the first thing someone looks at is your face, so the things that sit ON your face, like sunglasses, should add to the overall sharpness of your outfit/appearance, not detract from it.

How many sunglasses should I own?

I’ve been asked this quite a few times and I think you should own 2-3 pairs. This will ensure your sunglasses will look appropriate with whatever outfit you’re wearing – no matter what. While you can use just 1 pair, I would recommend at least two to be safe.

Do I need to match sunglasses to my outfit?

You don’t technically need to match them to your outfit, but there’s an argument to be made for it, which I’ll get into in the next section.

What color sunglasses should I have?

In order to cover you for all outfits and seasons, you should own a black pair and tortoise shell pair. If you want crazier colors then you should definitely get them, but only AFTER you’ve got the basics covered.

Black

You want a black pair because they go very well with more formal outfits and/or they match with your black accessories – i.e. your shoes or watch strap. To me, it’s not ideal if you’re wearing brown accessories – shoes, watch strap, etc, and then throw on a pair of black sunglasses, but it is still perfectly acceptable because it’s far enough away from these other accessories that it won’t ruin the cohesion of the look. If you only have 1 pair of sunglasses, you should go with black because it goes with any outfit you could be wearing.

Brown/Tortoise shell

This color goes very well with casual outfits, but also looks fantastic with a navy suit and brown accessories. Again, you can get away with black sunglasses with a navy suit, but it’s not ideal.

Any Other Color

If you want to have a crazy fun pair, then go nuts here, but just don’t wear it with anything but casual outfits, otherwise you could start look like Bruce Vilanch. Again, a well-dressed man shouldn’t have anything standing out in an outfit, he needs everything to work in perfect harmony to create an amazing whole. This absolutely applies to sunglasses.

Aviators – The Exception

If your face shape allows you to wear Aviators and you want to wear those, always go with a silver/charcoal metal frame and black/grey/green lenses as the default or “black” option, like I talked about above. For your “brown” pair of sunglasses, go with a gold metal frame and brown lenses. You don’t want a black or brown frame because it looks cheesy and deviates too far away the timeless look of Aviators.

What Color Lenses should I have?

This one is simple and the default lenses are usually great, but here’s my preferences:

Gradient – They look amazing and just give the sunglasses a nice, little extra touch of class.
Standard shaded/polarized – Most glasses will come with this type of lens that will probably match the color of the frame (black = black lenses, brown = brown lenses, etc.) and it’s perfectly acceptable, but if given the choice, I’d go with a gradient lens every time.

Anything outside of these lens colors and types, included mirrored lenses, are a no go. They’ll detract from the polished look of your outfit and this is to be avoided because your accessories should never overshadow anything else you’re wearing.

Don’t be this guy.

The best sunglasses for your face shape

The type of sunglasses you should own is dependent on you face shape. You generally want the shape of your sunglasses to be the opposite of your face shape, so they’ll help provide balance to your facial features.

A quick note about the below chart, including other resources out there – most of them will be talking about as many as 10 different face shapes and trust me, it’s a waste of time. There’s really only 3 face shapes that every man falls into:

Round
Oval
Square

Everything else is just nit-picking to fill up space on a website or magazine. The one that drives me the craziest is heart-shaped – that’s just an oval face with a wider forehead. If you’re considered heart-shaped according to the charts below, then just go with my oval suggestions.

You’ll notice that, outside of Aviators, I’m not recommending any frame-less style sunglasses and that’s because I think they just don’t look that great and never put my clients in them.

As for how to determine your face shape, the best resources I’ve found are from good ol’ LensCrafters and FramesDirect:

Round Face

If you have a round shaped face, you want to avoid round frames and go for more square/rectangular frames (i.e. Wayfarer style) or teardrop frames like Aviators. These styles will help give your face some dimension and break up the roundness, which is a good thing!

A quick note about why I don’t recommend Ray-Ban’s classic Wayfarers: I hate the angle of the lenses on them. Yes, they’re classic, but that still doesn’t mean they’re good. Notice how the frames are resting on the cheeks in the below picture? It’s annoying as hell and just looks bad on everyone.

Designer Options

Oliver Peoples Jack Huston Sun in Black + G15 Polar Glass

Oliver People Jack Huston Sun in Cocobolo + Bourbon Polar Glass

Barton Perreira Hopper in Black

Barton Perreira Hopper in Raven Tortoise Gradient

Gucci GG2269 in Grey and Brown

Saint Laurent Aviators in Gold

Oliver Peoples Brodsky in Sandalwood + G-15 Polar Glass
Barton Perreira Hopper in Black
Saint Laurent Aviators in Gold

Budget-Friendly Options

Warby Parker Winston in Jet Black

Warby Parker Winston in Old Fashioned Fade

J. Crew Irving in Black

J. Crew Irving in Soft Tortoise

Aldo Draude in Silver

J.Crew Jack in Gold

Warby Parker Winston in Jet Black
I love the classic, square shape of these sunglasses. For the price point, they don’t feel cheap or heavy.
J. Crew Irving in Soft Tortoise
J. Crew Jack in Gold

Oval Face

For this face shape, you’re lucky, because you have the most choices for sunglasses. You can wear round, square/rectangular, or rounded square-shaped sunglasses. The one thing you want to do is make sure the frames are as wide as your face – this is very important! Otherwise, it’ll look like you’re wearing kid sunglasses. Also, don’t you ever wear teardrop frames, like what most aviators have, because it’ll also make your face appear long or droopy.

Designer Options

Tom Ford Snowdon in Shiny Black

Tom Ford Snowdon in Havana

Oliver Peoples Masek Matte Black + Grey Mineral Glass

Oliver Peoples Masek Cocobolo + Cosmik Tone Glass

John Varvatos Grand in Black

John Varvatos Grand in Tortoise

Tom Ford Snowdon in Shiny Black
Fun Fact: Daniel Craig wore these in Spectre. If you have a round or oval face, these Tom Ford sunglasses are one of my all-time favorites! Everything about these square frames – the color, timeless design, and overall weight – couldn’t be better. Also, they’re the perfect width for oval faces which is very important because they’ll look disproportionate if they’re not as wide as your face.
Tom Ford Snowdon Sunglasses in Havana
Oliver Peoples Masek Sunglasses in Matte Black + Grey Mineral Glass
Oliver Peoples Masek Sunglasses in Cocobolo + Cosmik Tone Glass
Think of these Oliver Peoples sunglasses as the rounder version of the Tom Ford frames.
John Varvatos Grand in Black
John Varvatos Grand in Tortoise

Budget-Friendly Options

AJ Morgan Round Sunglasses in Matte Black

Topman Tortoise Shell 50s Style

Warby Parker Downing in Jet Black

Warby Parker Downing in Walnut Tortoise

Topman Matte Black Sunglasses
Warby Parker Downing in Jet Black
Warby Parker Downing in Walnut Tortoise
The thinness of these plastic frames compliment its round shape and are great for men with oval or square faces. I also like that they kept the arms thin because some designers would go with wider arms which would make these frames look unbalanced. These aren’t as wide as the Tom Ford and Oliver Peoples frames that I recommend above, so if you do decide to try these out, then make sure they’re the proper width for your face.

Square Face

For this face shape, you should look for round or teardrop frames. This will soften and balance your angular features. Avoid square or rectangle sunglasses because they’ll literally make you look like a block head

Designer Options

Persol Sunglasses Suprema PO3007S in Black

Persol Sunglasses Suprema PO3007S in Tortoise

Oliver Peoples Finley Esq. Sun in SMBK Moss Tortoise + Graphite Polar

Oliver Peoples Finley Esq Sun in Hickory Tortoise + Cosmik Tone Mineral Glass

Gucci GG2269 in Grey and Brown

Saint Laurent Aviators in Gold

Persol Sunglasses Suprema PO3007S in Black
Persol Sunglasses Suprema PO3007S In Tortoise
I love how sleek these frames are! The shiny finish and metal detailing on the arms adds to its sharp design. These are the perfect pair of sunglasses for men with square or oval faces.
Oliver Peoples Finley Esq. Sun in SMBK Moss Tortoise + Graphite
Oliver Peoples Finley Esq. Sun in Hickory Tortoise + Cosmik Tone Mineral Glass
Similar looking to the Persol sunglasses, the finish on both colors is matte and they’re slightly smaller in design.
Tom Ford Erin Aviator-Style Leather-Trimmed Gold-Tone Mirrored Sunglasses
Prada Aviator-Style Metal and Acetate Sunglasses

Budget-Friendly Options

Warby Parker Percey in Charcoal Fade

Warby Parker Madison in Whiskey

Ray-Ban Aviator at Collection in Gunmetal

Ray-Ban Aviator at Collection in Gold

Warby Parker Percey in Charcoal Fade
I LOVE the black to grey coloring of these frames. They look so expensive for what you’re paying for and I appreciate the simple, thin design which softens (in a good way!) the sharper features of a square-faced man. And they’re incredibly lightweight.
Warby Parker Madison in Whiskey
Ray-Ban Aviator at Collection in Gunmetal
Ray-Ban Aviator at Collection in Gold
Ray-Ban aviators are a timeless, iconic design that’s perfect for this face shape because it helps break up your angular features with the teardrop design.

Sunglasses Outfit Inspiration

(LOTS of inspiration images are also in my Summer Essentials Ebook)

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Polo-Shirt-Ashley-Weston-Mens-Clothing-Fit-Guide

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Men’s Leather Briefcases & Messenger bags

Okay, so the title is a bit click-baity. I’m sorry, but it’s time we got something straight. There is no scenario when you should be using a messenger bag – unless, of course, you’re a messenger. A messenger bag is the lazy/schlubby version of a briefcase with a removable shoulder strap. Messenger bags look horrible on their best day and any self-respecting man should avoid them. A modern briefcase is much more versatile and works in nearly all casual and dressy situations because of one simple thing: the removable shoulder strap. That little strap instantly turns a briefcase into a classy shoulder/messenger-type bag.

So if you’re hoping to see me talk about messenger bags and won’t consider using a briefcase with a shoulder strap instead, then:

Your briefcase should:

Look classy and timeless as hell – as always
Be free of logos, contrast stitching, flourishes or patterns or needless shine – they’re tacky.
Not be big enough for you to sleep in. – If you need that much stuff, it’s time to sit down and think about your choices in life, or go for a straight up utility item specifically built for this purpose. I’m thinking of those rolling briefcases that lawyers carry.
Carry a 15” laptop easily plus a good amount of items/paperwork, etc.
Have a removable shoulder strap and permanent handles.

Just like your weekender bag and leather backpack, the goal is to have something that shows you’re a man who cares about details and who values the items he chooses to carry with him.

What Material Should A Briefcase Be

In all my testing, the best looking and longest-lasting material is hands down leather. Any other material will stain or wear too easily. I’ve even tested some leather alternative briefcases and they just don’t compare.

What Color Should It Be

You want to stick with black or brown. I’ve looked into blues and gray briefcases and I can assure you that those colors will not age well, both from a style and durability perspective. So please, go conservative with your color choices here. You’ll thank me now and when you realize it’s been 10 years and you’re still carrying the same awesome briefcase.

You may have noticed in my weekender and backpack stories that I said to make sure they’re the same color because they will likely be carried together during trips. This rule can also apply to your briefcase if you’ll be using/carrying it more than a backpack.

When to use the shoulder strap

Just like I said in my backpack story – if you’re wearing a suit, blazer or sport coat, you should never use the shoulder strap. To do so will, at best, wrinkle the shoulder, possibly the lapel, and the back of your jacket. At worst, it’ll ruin the padding in the shoulder. If you’re wearing an unstructured jacket or more casual items, then that’s when to use the shoulder strap.

If you’re not using the shoulder strap, please take it off and keep it in the briefcase or at home.

The Best Leather Briefcases

Frank Clegg Zip Top Leather Briefcase

Buy the Frank Clegg Zip Top Leather Briefcase

Just like his weekender bag, this is my hands-down favorite briefcase of the bunch. It’s the same, high-quality leather, awesome hardware and a basic but well-thought out design. LIke all his products, it comes with a lifetime guarantee against any defects.

One of the things I really love about this briefcase is the hidden shoulder strap hooks on the sides. So if you remove the strap, no one would even know that it can be carried over your shoulder. I also love the side pockets on the front and back for slipping things in and out of quickly. It’s just a perfect briefcase in every way.

I have the double gusset version in my video, but the single gusset is also incredibly nice and roomy. I love that there’s options for sizing between single to triple gusset that you usually don’t find with most other brands.

If you pick up this briefcase, please also make sure to get it monogrammed. It just adds that little extra touch of class.

Coach Metropolitan Slim Brief

Buy the Coach Metropolitan Slim Brief

For a more budget-friendly item, I really, really like this one by Coach. They always do a great job with their leather goods, but I have to say, they knocked it out of the park here. The leather feels great, the shoulder strap hooks aren’t hidden like with Frank Clegg’s bag, but they can be tucked into the front and back pockets to be a little more hidden, which is nice.

The interior pocket lining is very soft, almost like a microfiber. The side pockets are also lined with this material. It’s hard to not keep touching it. The shoulder strap could be all leather, but since it’s cheaper than the Frank Clegg briefcase, I’m fine with using some cloth in the strap.

Also, the logo is simply stamped into the leather, and it’s at the bottom of the bag, so major, major points for this. Normally, Coach (and a lot of other brands) would have it placed a little more prominently near the top, but I’m glad they chose the bottom, otherwise this briefcase might not have made the cut.

The one major knock I can give this briefcase is that it has metal feet on the bottom. If you saw my weekender story, then you know that they tend to get scuffed and pitted, which will scratch anything you set these feet on. But just like with the weekender bag, wrap some electrical tape around the feet and it shouldn’t be too much of an issue or be visible.

Over all, I was very impressed though.

Notes about the state of briefcases

So just like with leather backpacks, the pickings are extremely slim in this category, but these are honest-to-goodness the best picks out of the bunch. Everything else was either very cheap or tacky looking or ridiculously expensive for a reason that I couldn’t tell in my testing. Check the Honorable Mentions section below for details about the bags that just missed the cut in case these two don’t meet your requirements.

Honorable mentions

Shinola Slim Briefcase

Buy Shinola’s Slim Briefcase

Love their leather and I like this one a lot, but it’s not as structured as I normally prefer a briefcase to be. So that’s why it wasn’t included.

Uri Minkoff Fulton Brief

Buy Uri Minkoff’s Fulton Brief

It looks good for the price, but I thought the quality of the leather was a little iffy. I’d spend a little extra and get the Coach bag, if my budget allowed.

Mulberry Heathcliffe Briefcase

Buy the Mulberry Single Document Holder Briefcase

I’m a huge fan of Mulberry, but honestly, they’re about the same price as the Frank Clegg briefcase and I would go for the Frank Clegg 100% of the time.

Jack Spade Barrow Leather Slim Briefcase

Buy Jack Spade’s Barrow Leather Slim Briefcase

I wasn’t the biggest fan of the floppy handles and that extra zipper on the bottom is pretty non-sensical.

Men’s Leather Backpack

Like I mentioned in my article and video about weekender bags, a leather backpack is a necessity for every man because it’s the type of bag that fills a lot of gaps in your bag arsenal – like when you work in a more casual environment and a briefcase would be a little odd. Or when you need a bag for groceries, going to the coffee shop or you’re going on a trip and putting your laptop and other personal items in a weekender bag won’t fit or will be a little too rough on them.

You want your backpack to do a couple of things:

It should look classy and have a timeless design.
It should work with dressy and casual outfits (not with suits, though, more on that in a minute)
Hold at least a 15” laptop
Should be comfortable – of course.
Should last you a long time

I think a lot of guys assume that a backpack is the one bag they need, no matter what they’re wearing and doing. This is mostly true, but with two massive exceptions.

If you’re wearing a suit or blazers often, then a backpack should never be worn with any of these outfits because the shoulder straps will ruin the shoulder pads and wrinkle your jacket all over the back. Wearing suits or Blazers = carrying your bag by the handles and never anything else – which means you need a briefcase. Unless you’re going for the IT guy look, please don’t wear your backpack (or messenger bag!) with these outfits. Even a nice backpack, like the ones I’ll be highlighting, won’t look right with those types of outfits.
If you’re needing a backpack for camping, lugging around your camera equipment or things like that, then you’ll need a specialty bag/backpack. You wouldn’t take a sedan off-roading, so please don’t do the same with your backpack. So if you have specialty items you need to carry around or are wearing suits or blazers often, then you need a bag specifically designed for those contexts – like a briefcase or camera bag.

What Material Should Your Backpack Be?

If you’re looking for something classy and functional, leather is the only option. Don’t get me wrong, I’ve seen some nice fabric or nylon ones, but they just don’t look right in as many scenarios as a leather backpack and they’ll wear or stain very easily.

Remember, you want your accessories to show you’re a man who cares about the details, and wearing a great outfit with anything but an equally classy backpack just looks like you missed the mark a bit. Think of those college kids you see with their Swiss army backpacks and sloppy suits running around conferences.

What Color Should You Get?

I like black, gray or cognac. But remember, as I said in my weekender bag story, this is the only time you need to match your accessory to another accessory – so whatever your weekender bag color is, your backpack should be a similar color. It doesn’t need to be perfectly matching, but black for black, brown for brown, etc. The reason for this is because your backpack will often be carried with your weekender on short trips, so you want some cohesion here.

I would honestly go for black because brown tends to show a little more scuffs and scratches, but if you really want to work a nice patina into a backpack, then there’s definitely no substitute for a brown backpack.

The Best Men’s Leather Backpacks

So let me tell you the state of the classy and timeless backpack industry or genre right now: It’s pretty awful out there. There’s so much crap out there. I’m not kidding when I say that just in the last year, I’ve tested at least 50 backpacks from every major and minor designer out there. There are so few brands that make a clean, nicely-designed and sharp looking backpack that won’t look silly or dated within a year or two. Aside from the ones I’ll show you, every other backpack missed the mark in some way or another.

This Is Ground – Venture Backpack

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Buy the Venture backpack

You might remember these guys from my wallets video/article and they’re back with hands down, the best leather backpack I’ve ever tested. The design is simple, classy and very well thought out. The Italian leather is really soft and supple with just enough stiffness to maintain the shape well. It’s just really nice to hold and use.

It has a lot of pockets and slots for all your items, including cables and chargers without feeling like it’s wasting space. It has two main compartments, one that is padded for your laptop and tablet or notebook, as well as some awesome pockets along the opposite side. Then the second big compartment is nice and wide open for whatever you want to put in there. I also really like this top zipper slot for your phone or wallet that is deceipity deep. My clients said they really liked this feature.

I know it sounds small, but their shoulder straps and back padding are the perfect width and very soft. I was worried that the thinner shoulder straps would dig in if there were some heavier items in the bag, but this isn’t the case.

A small point, but definitely a big deal for me, is where the shoulder straps are anchored to the bottom of the bag. See how they attach to the middle and bottom of the bag? This is awesome because it is supporting a good portion of the weight from the bottom of the bag, and not from the front side like most backpacks. I’ve definitely found other bags breaking, or the stitching coming loose at this exact point a few times, even after, what I’d consider, very light usage. While we’re talking about the straps, I love how they don’t have a bunch of extra slack on them. Even if you tighten or loosen them, you don’t have a bunch of excess strap flapping around. This is super annoying on a lot of other bags. Besides, your backpack should sit relatively high on your back, not on the lower part of your back or worst-of-all, your butt. I’m glad that This Is Ground knows this and doesn’t even give people the option!!

And if this bag wasn’t cool enough, it has a special, secret compartment in part of the bag for you to hide your valuables as well as the included Tile dongle, so in case you ever lose your bag, you can track it via the app.

I have it here in their cognac brown, which has such a nice, rich color and will just get better with age. But I also really like their charcoal black as well. Also, make sure to get the regular size, the mini size is small by a few inches and is much more geared for a woman.

KILLSPENCER – Special Ops Backpack 2.0

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Buy the KILLSPENCER Special Ops Backpack 2.0

If you want a backpack with a little more tactical edge to it, then the KILLSPENCER Special Ops Backpack is right up your alley. Just like with their weekender bag, their leather is really damn good. I especially love that they have it in this really nice Charcoal Gary color, which matches their weekender’s color perfectly. They also have it in black, which I also like a lot, they also make a nylon version, so it’s a great leather alternative bag, as well.

A note on the color in the image above – watch my video showing this backpack because that’s the actual, true life color. For some reason these images don’t represent the color correctly.

Like all their products, the design is well-thought out and classy and just like the Venture Backpack, their zippers are buttery smooth and the rest of the hardware is great.

The big pocket on the front is nice to have, but I’m not sure how safe it is if you’re utilizing it in a crowd. I know I’d be a little nervous keeping some valuables there.

The lining is also water and fireproof, so if you spill something inside (hopefully not), it won’t be such a disaster, for the bag at least. Another nice touch is the mesh interior pockets, which allow you to see what’s inside them. It sounds small, but trust me, it’s a very nice feature to have.

Matt & Nat – Dean Backpack

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Buy the Dean backpack

If you’re looking for a leather alternative backpack, then I really like this one by Matt & Nat. Out of all the faux leather backpacks I’ve seen, this is definitely the best.

I really like the unique but not overbearing design and the hardware is surprisingly nice and smooth. It has a big top-loading storage area, with a laptop compartment and an extra pocket as well. It also has this outter pocket for some of your smaller items which is nice to have.

The only downside is that the woven straps feel a little cheap and I don’t know how durable this bag is in the longrun, but for a relatively cheap bag, this is perfectly acceptable.

I have it here in black, but I also like their brown color, which they call chili. So if you’re looking for a leather alternative backpack, this is the best I’ve seen – by far.

Honorable Mentions

Valextra V Line Backpack

Buy the Valextra V Line backpack

I liked it a lot, just like their wallets, but unfortunately it’s structure is too stiff and it looks like other designer bags that I just think look odd. It’s like wearing a box on your back, as opposed to something that’ll mold a little better to your body and it’s contents. It also just has one big compartment, with a pocket for a laptop and nothing else, which is a little annoying because then all your stuff will be banging around in it, or you’ll need some sort of organizer to then put into the backpack.

COTE & CIEL RHINE COATED CANVAS AND LEATHER

Buy the Cote & Ciel Rhine backpack

It’s just a little too tactical looking for my taste. The front also looks like a little bit of a sad emoji. But for utility purposes, this bag is great! But it won’t fit a whole lot of stuff inside.

AER Fit Pack

Buy the Aer Fit Pack

Even though it’s not leather, I really love this backpack because it’s so utilitarian. This is the perfect gym backpack, though, and even has an extra compartment for your shoes, which comes in handy a lot.

Mulberry Multitasker

Buy the Mulberry Multitasker backpack

Love their leather products, including their weekender bag, and this one can be used as a shoulder bag and top handle bag, but it’s a little bit small in dimensions and just has a big pocket to put everything in. Organization isn’t so great with this one and it’s slight on the smaller side. While my top choices are 17” or more in height, this one is 15” which is right on the edge of looking like a girl’s backpack.

So that’s it. Those are honestly the best backpacks I could find – anywhere in the world. I’ve been working on this story for ages and I was shocked to discover these were the only ones good enough to recommend. Everything else was a weird size, didn’t have good storage, had a big ass logo on it, crazy contrasting stitching or just something was off about it. If you make leather backpacks and want to prove me wrong, then please contact me and prove me wrong!

Weekender Bag

A weekender bag, or as some people call them – leather duffle bags – are an essential every man should have because like every wardrobe item and accessory you own, it should serve a purpose and look damn good at the same time. A weekender bag’s purpose is to fill the void left when a backpack would be too small and a large piece of luggage would be too big.

If you’re like a majority of my clients (and I, as well), who typically go on shorter trips of up to a week at a time, you’ll be using your weekender more than any other piece of luggage you own.

The requirements for a weekender bag are:

Clean, classic design that is beautiful and functional
High quality construction that’ll last many, many years
Meets the airlines’ carry-on luggage size requirements
Not have too many rivets, embellishments or a tacky logos all over it. 99% of weekender bags fail this test in one way or another by looking too utilitarian or like a billboard for the brand. A gentleman doesn’t need to advertise the brands he owns. It’s low rent.

When to Use a Weekender Bag

You would think this one would be simple, but I see a lot of guys using their weekender bags incorrectly. So let’s go over when you should and shouldn’t be using your weekender bag.

Do use your weekender for:

Going on shorter trips, up to a week at a time.
Any travel when you don’t need your full-sized checked luggage or when a backpack/messengers is too small.

Don’t use your weekender As A

Gym bag

I can’t tell you how many guys I see walking out of the gym with their weekender bags. They’re way too big and nice to be shoving in and out of lockers. If you need a gym bag, get one, or, like I’d suggest, use a backpack instead.

Everyday or work bag

These are not to be used for work. There’s other bags, like a briefcase or messenger bag, that are built for this. And don’t use this bag in place of a tote bag for grocery runs, shopping, etc. it’s definitely not meant for that. You’ll ruin it!

Garment bag

If you need to carry suits or other delicate items, that’s what a garment bag is for. I’ve seen a few weekender bags that have garment bags built into the them and I have to wonder who would put a suit into their duffle bag, and THEN stack a bunch of stuff on top and on the sides of them?

You’re just asking for a horribly wrinkled, or worse yet, ruined suit by doing this. If you need to transport a suit or delicate clothing item, put it in a garment bag and carry it separately or pack it gently into your larger (not overflowing) checked luggage where it’ll have a little bit of space. Weekenders are not the do-all, be-all bags, so please don’t treat them like one.

What Color Should You Get?

Just like anything you carry, you want it to look amazing, so sticking with the clean, classic colors of black, brown or gray is what you want. Any other colors or crazy patterns will not age well and come and go as fashion dictates. If I had to choose, I’d say go with black because browns can tend to show scratches and marks a little more, where black wouldn’t show them as much, that way your bag will look newer for longer. But if you like the aged patina look of a brown bag, that’s perfectly fine as well.

How to match your weekender bag to…

This has been asked a few times, so I want to address how you would match your weekender bag to your other accessories or outfits.

Since we’re sticking to the clean, classic colors, I’d say your weekender should match (doesn’t have to be perfect, just close) your backpack’s color. The reason is because you’ll likely be carrying it along with your weekender bag more than any other bags you’ll own, so a black weekender and brown backpack wouldn’t look so cohesive. If you instead go for a briefcase/messenger bag and don’t have or use a backpack, it should probably match your weekender if you’ll be carrying it along on trips.

As for your outfit, don’t worry too much about matching it to your outfit or other accessories because it’s not part of your outfit like your shoes, belts and watch straps are so it won’t interfere with the cohesiveness of your outfit.

And if you were thinking about asking: Yes, your weekender will look great with casual or dressy outfits, that’s why I consider it an essential.

Quick Tip

When storing your weekender bag, I find that they’re great for storing your scarves, gloves, dress shoes and other items in. Since the bags I’m recommending have some structure to them, they’ll start losing this structure if you’re shoving them under your bed or into a dresser. That way, you can maintain the shape and utilize the empty space.

The Best Weekenders Bags

Please note that all my recommended weekender bags come in multiple colors (including brown), even though I’m only showing them in black or gray, so click through the link to see details and the color options.

Frank Clegg Signature Travel Duffel

See details & buy the Frank Clegg Signature Travel Duffel

This is one of my all-time favorite weekender bags for a few reasons:

The styling is beautiful and classic.
The leather is gorgeous, supple, durable and it has just the right amount of structure to it.
The flap that hides the zipper really distinguishes it against the sea of similar-looking weekenders.
It’s zipper allows it to open extremely wide – this is very rare with most weekenders.
Their customer service is amazing (see the video or below for the story about this)

I had a client who needed a weekender bag super last minute for a press tour. So I called the number on the Frank Clegg website and was expecting a customer service person to pick up, because they’re not a small company, so a man with a super thick Boston accent picks up and says “Yeah, this is Frank”. It honestly took me a few seconds to say something because I was so surprised he actually picked up the phone! I explained the situation and he had a custom bag, including monogram out to me that afternoon for morning delivery. Talk about service!

The last thing that puts Frank’s bag head and shoulders above the rest is that all his items come with a lifetime warranty against any defects. If anything every happens to your bag and needs a repair, call or email Frank and they’ll fix it free of charge. I haven’t seen that with any of the other bags worthy of testing in all the years I’ve been searching.

KILLSPENCER Weekender 3.0

See details & buy the KILLSPENCER Weekender 3.0

Out of all the bags I’ve tested over the years, this is the best gray bag I’ve ever seen. The color is just the right shade of gray to not be obtrusive and I also really like the black handles and accents, so it allows you to choose a black or gray backpack to go with it, which are both great choices.

Like all their stuff, it has a little military edge but still remains timeless and classy.I really like that about them – it’s what sets them apart.

If you follow me on SnapChat, you saw Spencer gave me a tour of the production facility and showroom. I’m so impressed by quality of their leather and I honestly think this bag is worth more than they’re charging for it. I also like that it doesn’t have metal feet on the bottom, which can be an issue that I’ll discuss with my next recommendation.

The one unique thing about the bag, which I really liked, is this handle on the side. If you’ve ever struggled with pulling bags out of overhead bins, then you know how valuable this handle is in that situation.

I love that they manage to make high-quality products at an awesome price point.

Mulberry Clipper Leather Holdall Bag

See details & buy the Mulberry Clipper in Black or Brown

This is the first weekender bag I saw, before I was a Celebrity Menswear Stylist, where I instantly understood what people meant when they said luxury leather goods. Holy sh*t is this bag gorgeous in person. It also has that iconic weekender/duffle silhouette that’s never been done better. The leather is so soft and supple and dare I say… delicious?

The only knock I have against this bag is the metal feet on the bottom. You have to be a little more careful about what you set this bag on because if the feet become pitted or scratched, it start scratching any surface you put this bag on – wood floors, tables or car roofs and hoods. A simple fix for this is to put a little electric tape around the metal feet every so often so they don’t get scratched up. To me, that’s a small inconvenience, that no one will ever see, for an amazing weekender bag.

Budget Friendly Options

Combatant Gentleman Black Leather Duffel Bag

See details & buy the Combatant Gentleman Black Leather Duffel Bag

At this price point, I haven’t seen a better leather duffle bag. The problem with most bags at a similar price point is that they have really bad designs because they don’t want to use large swaths of leather because that’s more expensive to source and produce. But I think this weekender toes that line very well.

There’s two small things I’d love to see changed on this bag, though.

The zipper should go all the way to the end of the bag, so it’s easier to load and unload the bag’s contents. So when pulling out, say, your dopp kit for the security line, you’re going to have to pack it right in the middle, otherwise you’ll have a hard time pulling it out if it were on either end of the bag.
It has metal feet, which, like I discussed earlier, can be a problem. But a quick fix is to put some black electrical tape on them.

Outside of that though, for the price, I wasn’t able to find something as clean looking or well-made. So kudos to the Combatant Gentleman team for pulling this off.

Everlane The Dipped Weekender

See details & buy Everlane’s The Dipped Weekender

My second favorite budget-friendly weekender is the Everlane Dipped Weekender. The best feature of this bag, and why it’s the only canvas bag I’ll recommend, is the coated bottom. The problem with other canvas weekender bags is that if you set it down on a dirty or wet surface, this bag would look dirty or be completely soaked, including the items inside, very quickly. With the coated bottom, you avoid this.

Another major bonus is that it doesn’t have any branding on the outside, which plagues a lot of bags at this price point, and the stitching and leather is very high quality. And lastly, if you don’t know about Everlane’s 100% transparent business practices, you should look them up. They’re pretty revolutionary in this respect.

The major downside is that it doesn’t have a shoulder strap, but the two main handles are actually long enough to be used as a shoulder strap, so I wouldn’t consider this a deal-breaker.

Honorable Mentions

These are the weekender bags that just missed the mark for one reason or another.

Coach Explorer Bag 52

See details & buy the Coach Explorer Bag 52

If you want a bag similar to the Mulberry Clipper but cheaper, this is the weekender bag for you.

Shinola Signature Duffle

See details & buy the Shingle Signature Duffle

This one didn’t make the cut solely because it goes in and out of stock pretty regularly. The company has assured me that their stock problems will be fixed soon, but since it’s not readily available, it’s hard to recommend. If you can find it, this would very easily be near the top of my list.

Uri Minkoff Wythe Weekender

See details & buy Uri Minkoff’s Wythe Weekender

I like this one a lot, but I found it to be slightly expensive for what you got and I had two minor quibbles with the design:

The way they reinforced the bottom could have been done better without using those big hunks of leather on each side.
Even though the leather looks pebbled and matte in the above image, it’s quite a bit more shiny in person. Right on the border of being a little too much for my taste.

Matt & Nat – Artigan

See details & buy Matt & Nat

This one’s a bit of an outlier because it’s very structured compared to the others, but I liked that about it. The main selling point is that it’s a very well made vegan bag option and has a great price point. So if you’re looking for a leather alternative or want something with more structure, then this one is for you.

That’s it, those are the best weekender bags I could find in many, many years of searching for the perfect ones.

Best Undershirts For Men

If you own any of the collared shirts I recommend in my Men’s Wardrobe Essentials Series, specifically the Oxford Button Down Shirt and a Semi Spread Collar dress shirt, you need to own some crew and v-neck undershirts. And before we get into it, there’s no scenario when you should ever wear a tank-top undershirt, AKA a wife beater – ever. You’ll see the lines underneath any shirt you’re wearing, and it just looks terrible. So let’s talk about the best undershirts for men and why you should own them.

Undershirts are essential because

They provide a barrier between your sweaty, oily, deodorant-riddled skin and your dress shirts.
Due to this barrier, you may not have to get them cleaned as often, which will prolong their life.
They make dress shirts, specifically light-colored ones, look much better by not showing your skin and/or nipples through them.
They add another layer to your outfit for a little extra warmth or moisture wicking – depending on the weather.

How to Wear an Undershirt Under a Dress Shirt

You would think this is simple, right? Me too, but it’s very rare when a client knows how to wear an undershirt properly. A good undershirt is not something anyone should ever notice. If it’s noticeable, you’ve failed.

These are the 2 rules for wearing an undershirt:

If you’re wearing a collared shirt without a tie, with the top button or two open, you need to wear a v-neck undershirt. Remember, no one should ever see your undershirt – even a bit of the collar.
If you’re wearing a tie, you have to wear a crew neck undershirt. Otherwise, you’ll be able to see the v under the shirt and it looks like crap.

When should you go without an undershirt?

The only time I’d suggest not wearing an undershirt is if you’re wearing a white collared shirt. If you’re a lighter skinned guy, this is more geared toward you. Because most other undershirts might be seen through. But you can still try wearing a nude or gray undershirt to see if it’s not visible.

This problem isn’t as bad if you’re darker-skinned and wearing a similar-colored undershirt. That said, if you have darker nipples or nipples that tend to stick out a little bit, then an undershirt is required for you no matter what. Just make sure it matches your skin tone relatively closely.

Are Undershirts Supposed to be Tight?

A lot of my clients ask this question and the short answer is:
Sort of.

They shouldn’t be skin tight, but they should absolutely fit close to the body. Ideally, you want an undershirt to fit this way in the body and sleeves so you don’t see wrinkles or creases underneath your shirt. If the sleeves or body is loose, you’ll definitely see the line under the sleeves and wrinkles in the body – no matter the color of shirt you’re wearing over it.

Are Undershirts Supposed to be Thin?

Yes! They should be thin because they’re an underlayer and a thinner shirt will feel better and not add bulk to your frame. You don’t want this to happen regardless of your body type.

Should I have only white undershirts?

Not necessarily. I always have my clients wear undershirts that are closer to their skin tone. So if you’re darker skinned, you can go with a darker gray, brown, or black undershirt. Lighter skinned men should stick with light gray or white. A warning though, if you’re lighter skinned: a light gray undershirt under white or light-colored shirts is ok, but honestly, I’ve tried this a few times it and it tends to make the dress shirt look dingy or kind of faded. It’s not a good look, so I usually say to go without an undershirt in these instances.

Another quick note while we’re talking about white undershirts

I see this often with guys – if I can see exactly where your undershirt starts and ends around your neck or sleeves, (this only happens with light blue and white collared shirts), this means your shirt’s fabric is too thin and/or you need to change the color of your undershirt to match your skin tone better.

The Best White and colored Undershirts

These are the best undershirts that my clients and I love the most. Having tried all the major ones out there, these are my favorites:

Tommy John Second Skin Undershirts

Buy Tommy John’s Second Skin Crew and Deep V-Neck Undershirts

Second Skin Crew and Deep V-Neck undershirts are my favorites. I like these a lot because they fit snugly on all body types and the fabric is super soft and has a little bit of stretch to it, so they won’t leave winkles showing through your shirts. But these niceties don’t come cheaply. Unlike their underwear, though, which I discussed here, they are very durable and will last you a good long while. They also make a nude and black colored undershirts to cover most men out there.

A quick note about their V-necks. Their images aren’t quite accurate and their titles are misleading.

Their “Deep V-Neck” is actually a regular v-neck length, so get that one and don’t waste your time with the regular v-neck, because the regular one is way too high and will absolutely be visible if you wear your collared shirts unbuttoned. I know the pictures look like the v is quite deep, but trust me, in person they’re not that deep.

RibbedTee Tri-Blend Undershirts

Buy RibbedTee’s Undershirts

RibbedTee makes some of the softest, most comfortable undershirts I’ve tested. My clients said it was like wearing a soft fluffy layer of air. Their gray undershirts are great for lighter skinned guys, too, but they make many colors. You honestly can’t go wrong with any of their undershirts, but my clients were partial to the Tri Blend, Supima cotton and their Evo Tencell ones.

Calvin Klein Undershirts

Buy Calvin Klein Undershirts

For a budget-friendly option, I really like Calvin Klein’s Cotton Classic undershirts because the fit is great and the fabric is not too thick or thin, which is a problem with most other undershirts in this price range.

I like them because they also have different fits based on your body type – like slim and regular – which fit my larger or taller clients very well. They also make a similar undershirt to Tommy John called Body Modal, but I say just spend the few extra bucks and get the Tommy Johns instead because they’re just all around better.

Spanx Undershirts

Buy Spanx Cotton Compression Crew & V-Neck Undershirts

I mentioned these in one of my AskAW videos because my clients who wear these LOVE them. If you’re looking to slim down your waist, belly or chest area, these are perfect. I like to say that they are like visual airbrushing tools. They’re not so snug that it feels like you can’t breath, which is important because I think a lot of men assume they’ll be too restrictive, but they’re just a little bit tighter than your average shirt, but they will literally drop you down a waist or shirt size in most cases.

Alright, that’s it. Those are the best undershirts for men – period!

Underwear – The Best Boxer Briefs

So let’s talk about your twig and berries, well… not really, let’s talk about the thing they go into – your underwear.

For a long time, men have viewed underwear as an afterthought. They were made of white cotton, reached up to your armpits, looked like you had a perpetual load in your pants and were bought in a 50 pack that’d last well into the next decade (or five, if you’re like my grandfather).

Other than shoes, underwear will impact your overall comfort more than any other garment. It doesn’t matter what you’re wearing on the outside, if you’ve got ill-fitting, bunching underwear, you’ll be annoyed and uncomfortable.

There’s a reason rough, uncomfortable clothing has been used for thousands of years as a form of torture.

The 2 Rules of Underwear Every Man Should Live By

Before we get into details, whether you go with my recommendations at the bottom of this page or not, these are the 2 rules for you should adhere to:

Color is very important.
Just like I mentioned in my 10 Style Mistakes Ebook regarding socks, you should never wear (or own!) white underwear. It’s gross looking, stains easily and reminds everyone of their father or grandfathers – and not in a good way. So stick with the dark, solid colors like black, brown, blue or charcoal gray and you’ll be fine.
Avoid logos as much as possible.
With some brands, including the ones I think you should own at the bottom of this story, it’s almost unavoidable, but please, please refrain from the ridiculous tommy logos and other crap like that. It’s just trashy.

Why You Should Only Wear Boxer Briefs

Underwear is an item of clothing that, if it’s doing it’s job correctly, shouldn’t be noticed. If you’re thinking about your underwear, even a second after you’ve put them on, that’s a problem.

There’s 5 major types of mens underwear

Briefs
Boxers
Boxer Briefs
Trunks
(Technically, there’s thongs too, but… no)

Underwear should not do the following

Bunch or dig into your leg or crotch.
Cause any chafing.
Create visible panty lines (VPL’s) – this is a problem for men, too!
Turn your undercarriage into a cheese factory.
Remind someone of their meth-cooking father or grandfather.

In my experience, there’s only one type of underwear that has the least amount of the problems listed above: boxer briefs.

This is why I only recommend the best boxer briefs to all my clients. They’re the holy grail of underwear for the following reasons:

Most comfortable fit
Great breathability
Keep your plums secure
Flattering on any body type which is important because you want a woman to still think you look sexy when you’re just in your underwear
Won’t show through clothing and/or create VPL’s.

The Best Boxer Briefs

Here’s the brands I recommend to all my clients, based on their needs and preferences and what I’d consider the most comfortable underwear for men.

Ex-Officio Give N Go Boxer Briefs

Buy Them Here

There’s two different pairs from Ex-Officio that I recommend. The Give N Go’s are the ones my clients love the most. I’ve never seen them get so enthusiastic about a brand, but they really do love these.

Pros

Super comfortable, soft fabric.
Moisture wicking, breathable, synthetic blend material.
Generous, almost drop-crotch fit.
Very little stretching after extended use.
Extremely durable – I’ve seen them last over a year of regular wear with very little breakdown in quality or fit.
They don’t bunch.
I like the smaller waistband a lot, since it won’t be sticking out the top of your pants as much as some other brands.

Cons

They definitely look “sporty”, especially with the logo on the waistband.
If you prefer natural fibers, these are synthetic.
If you really like your plums held tightly in place, like with briefs, these will feel a little loose in that area. They feel more like boxers since the crotch is cut lower.
Some clients don’t like the odd angled stitching along the butt, they say it feels a little weird. But others say they prefer it.
The pocket access is through the side, which is the norm, but there’s another brand that I think does this better, which I’ll get into shortly.

Ex-Officio Give-N-Go Sport Mesh 6 or 9 Inch Boxer Briefs

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These are similar to Give and Go’s, but my clients that didn’t like the regular ones, preferred these because:

The material is softer and silkier, but some of them also noted that this silkyness led to some bunching around the upper thigh as the day wore on. The best way to mitigate this is by getting the 6 or 9 inch versions depending on how tall you are.

The pouch/pocket in the front is smaller and tighter. These are their sport version. So if you really like your plums kept snug, these are better for you.
The downside is the loud colors and contrasting stitching. I personally think it’s a bit much, but my clients loved the fit and material so much that I’m willing to make an exception here because I want you to be as comfortable as possible. Just make sure to get the black ones with the red stitching – the other colors are way too loud.

Tommy John Second Skin Boxer Brief

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If my clients didn’t like the Ex-Officios, they gravitated towards these, instead.

Pros

Super soft material – the softest of the bunch, by far.
A top-loading pocket design that’s easier to use at the urinal.
Very breathable.
Comfortable waistband.
Snug applebag fit.

Cons

They’re pretty damn pricey – $30+ a pair.
They don’t retain their shape very well after extended wear, which can lead to a little bunching in the legs. To avoid this, I’ve had clients go down a size, but after a little bit, they’ll stretch out perfectly.
Not as durable. You’ll definitely have to replenish your stock more often than with Ex-Officio. These usually last about 8 -10 months with clients before they start wearing thin in areas.
They are made of thinner material, which is kind of sheer, which adds to the less-than-durable point I just mentioned.

H&M Cotton Stretch Boxer Briefs

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I’m sure some of you are looking at the prices of my recommendations above and think I’m crazy. If caring about your genital comfort is a crime, then arrest me now!

My, let’s just say… “budget-conscious” clients prefer these over the other brands for the following reasons:

Pros

They’re cheap – $18 for a 3 pack.
Decent cotton fabric – not the best, but not the worst, either.
Doesn’t bunch as much.
No branding/logos- which is a big plus.
Did I mention they’re cheap?

Cons

Not as soft as other brands.
Not as durable and have a tendency to fade quicker than other brands.

Honorable Mentions

These just barely didn’t make the cut, but I wanted to include them as well. For their price, they’re great, but durability and longevity is always an issue at these price points. But if you really don’t want to pay a lot, these are right up your alley and hit the color and no-logo points perfectly. Just please replace them when they’re faded or holey. Typical usages was anywhere from 6 months to a year.

Uniqlo’s Airism Mesh Boxer Briefs

Uniqlo’s Supima Cotton Boxer Briefs

Kirkland Boxer Briefs

That’s it, those are the honest-to-goodness best boxer briefs that I use with all my clients. So get your sh*t together and start wearing the most comfortable underwear for men – boxer briefs! Your psyche and gentleman’s sausage (that’s 4 euphemisms for male genitalia, if you’ve been keeping track!) will thank you!