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:

ariGTFO

Your briefcase should:

  1. Look classy and timeless as hell – as always
  2. Be free of logos, contrast stitching, flourishes or patterns or needless shine – they’re tacky.
  3. 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.
  4. Carry a 15” laptop easily plus a good amount of items/paperwork, etc.
  5. 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

FrankCleggShoulderStrapHooks

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

CoachMetropolitanBriefcaseShoulderStrap

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

ShinolaSlimLeahterBriefcaseAshleyWeston

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

uri-minkoff-pebbled-leather-fulton-briefcase-Ashley-Weston1

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

MulberryHeathcliffeLeatherBriefcaseAshleyWeston

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

JackSpaceBarrowLeatherBriefcaseAshleyWeston

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:

  1. It should look classy and have a timeless design.
  2. It should work with dressy and casual outfits (not with suits, though, more on that in a minute)
  3. Hold at least a 15” laptop
  4. Should be comfortable – of course.
  5. 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.

  1. 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.
  2. 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

venture_cognac_4_1024x1024_Leather_backpack_Ashley_Weston

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

Kill_Spencer_grey_leather_special_ops1_1_2_Ashley_Weston

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

Matt_Nat_Dead_Leather_backpack_Ashley_Weston2

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

VALEXTRA_Pebble-Grain Leather Backpack_Ashley Weston

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

cote&ciel - RHINE COATED CANVAS AND LEATHER backpack Ashley Weston

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

Aer Fit Pack_backpack_Ashley_Weston

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

Mulberry Multitasker leather backpack _Leather_backpack_Ashley_Weston

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

Frank Clegg Signature Travel Duffel Weekender Bag Holdall Carryall Leather Black Ashley Weston

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

KillSpencer Weekender 3.0 Weekender Bag Holdall Carryall Duffle Leather Black Ashley Weston

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

Mulberry Clipper Leather Holdall Bag Ashley Weston Weekender Bag Black

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

Combatant Gentleman Black Leather Duffel Bag Holdall Ashley Weston Weekender 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.

  1. 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.
  2. 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

Everlane The Dipped Weekender Bag Holdall Bag Ashley Weston Canvas Black

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

Coach Explorer Bag 52 Weekender Bag Holdall Carryall Leather Black Ashley Weston

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

Shinola Signature Duffle Weekender Bag Holdall Carryall Leather Black Ashley Weston

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

Uri Minkoff Wythe Weekender Weekender Bag Holdall Carryall Leather Black Ashley Weston

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:

  1. The way they reinforced the bottom could have been done better without using those big hunks of leather on each side.
  2. 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

Matt Nat Artigan Weekender Bag Holdall Carryall Leather Vegan Black Ashley Weston

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.

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:

  1. 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.
  2. 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

  1. Briefs
  2. Boxers
  3. Boxer Briefs
  4. Trunks
  5. (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

ExofficioDropCrotchBig
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

Buy Them Here

 

ExOfficioSportMesh

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

Buy Them Here

TommyJohnLogoBlendIf 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

Buy Them Here

HMBoxerBrief

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

UniqloAirismBoxerBriefs

Uniqlo’s Supima Cotton Boxer Briefs

UniqloSupimaCottomBoxerBriefs

Kirkland Boxer Briefs

KirklandBlackBoxerBriefsUnderwear

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!

Phone/Mobile Cases

Just like with your wallets, a phone is something you’re probably carrying on a daily basis. So let’s make sure your case is as classy, well-designed and functional to meet your needs.

If you work in a more physically-intensive job, where utility trumps everything else, then use whatever case meets your requirements for the week and then grab one of my choices below for the off-hours or weekend. Because there’s nothing worse than seeing a guy with a big phone bulge in his front pocket, or worse-yet, a big ass phone clipped to his belt – yuck.

The goal with anything you carry, and especially your phone case, is to provide protection, while still looking sharp and being as small/minimal as possible. Believe me, I’ve tested a few hundred cases over the years and these are by far the best that my clients and I all agree about.

Quick note: Even though I’m demonstrating cases and showing pictures of cases for iPhones, I do my best to provide Android options wherever possible.

The Veil XT by Caudabe

Caudabe Veil XT Ashley Weston Phone Case

Buy it for iPhone | Similar for Samsung phones
This case is so awesome that not only do I recommend it to my clients, but I use it myself.

It protects the back and sides with the slimmest profile I’ve ever seen. Also, here’s a point I especially love – It doesn’t have some gaudy logo all over it.

It’s made of a flexible but hard plastic that has a rubbery matte texture, so it isn’t slippery like other cases. There’s lot of similar cases out there, but I like this one because it covers the bottom and top parts – which most others don’t. In my tests, if this type of case doesn’t cover all sides, the edges will catch on your pockets or fingers and the corners will chip off easily and become jagged, which is very annoying to hold.

The only downside to this case is it doesn’t provide any screen protection, so it’ll be sitting on the screen if you lay your phone face down. If you need screen protection, see the next two cases.

I also like that the case is still a little pliable. Most similar cases are very brittle and my clients broke a few of them trying them out for me. This one has come off and on numerous times and looks good as new and hasn’t warped yet.

Frost and Wisp are my two favorite colors.

Ringke Air & Slim Cases

RingkeAirSmoke RingkeSlim

Buy Ringke Air (A.K.A Fusion Air) | Buy Ringke Slim (both are available for Android phones)

Before I discovered the Veil, I recommended and used Ringke cases for years.

The Air case is made of a polyurethane material so it’s soft and flexible. The main advantage of this case is it has a little bit of a lip around the screen, so the screen is protected if you lay your phone face down or drop it. I also like the dust and lint flaps for the headphone and power plugs. They can be annoying if you use these plugs often, so definitely grab the Slim case instead, as it doesn’t have them.

The Slim case is the hard plastic version of the Air case, but, as I said above, without the dust and lint flaps.

I like the crystal clear as well as the smoke black colors for both because they show off the beauty of your phone without looking gaudy.

Bellroy Phone Case – 3 Card

bellroy-pcib-black-texture-web-01

Buy it here

If you’re looking for a relatively small leather case that can hold 3 cards as well, then grab the Bellroy 3 Card Phone case.

It’s made of the same leather as their wallets and feels really nice in the hand. It’s definitely the smallest phone/card case I’ve seen. They also make a version for 1 card, but what’s the point of that? And their similar case that holds no cards is just too bulky for such a single purpose item.

The major downside to this case, aside from the somewhat bigger size, is the price. It’s quite expensive at about $65, but again, it’s the best leather style case I’ve tested.

I holding one in Blue Steel in the video above, but I also like their Charcoal, Black and Java colors.
So those are the phone cases I recommend to my clients and personally use. Have any cases that you love and you’re not trying to hawk your own product? Leave a comment so myself and others can see. I’m always on the hunt for awesome products!