16 Accessories Every Man Needs

These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.

Have questions? Curious what others think?

Join us in the comments section of the video above.

16. White Pocket Square

Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.

White Pocket Square Ashley Weston

$175 – Tom Ford Solid Classic Silk Pocket Square
$60 – Boss Solid Silk Pocket Square
$10 – The Tie Bar Solid White Cotton Pocket Square

15. Silver Tie Bar

This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.

Silver Tie Bar Ashley Weston$15 – The Tie Bar Silver Shot Tie Bar
$70 – J. Crew Sterling-Silver Tie Clip 

14. Solid Black and Navy Tie

These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.

Black and Navy Tie Ashley Weston

$19 – The Tie Bar Grenafaux Tie (available in black and navy)
$60 – J. Crew American Wool Navy Tie
$60 – J. Crew American Wool Black Tie

13. Dress Socks

Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.

Solid or Patterned Dress Socks Ashley Weston

$4 – Uniqlo Argyle Socks
$20 – Brooks Brothers Egyptian Cotton Jersey Knit Crew Socks
$15 – J. Crew Tipped Microstriped Socks

12. Sunglasses

Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.

Sunglasses 1 Ashley Weston 2

$415 – Tom Ford Snowdon Sunglasses
$98 – J. Crew Jack Sunglasses
$95 – Warby Parker Winston Sunglasses 

11. Baseball Hat

We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.

Baseball Cap Ashley Weston

$48 – Gents ‘The Directors’ Baseball Cap
$22 – Flexfit Blank Snapback 2014

10. Black and Brown Oxford or Derby Shoes

Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.

Black and Brown Shoes Ashley Weston

$395 – Allen Edmonds Carlyle Plain-Toe Oxfords
$750 – Prada Plain-Toe Bluchers
$175 – Johnston & Murphy Melton Cap Toe Oxfords

9. Black and Brown Dress Belts

Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.

Black and Brown Dress Belt Ashley Weston

$98 – Brooks Brothers Leather Dress Belt
$98 – Allen Edmonds Poplar Dress Belt
$25 – H&M Leather Belt

8. Weekender Bag

Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.

Weekender Bag Ashley Weston$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)

7. Dopp Kit

This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.

Dopp Kit 1 Ashley Weston 2

$148 – Jack Spade Mason Leather Zipper Top Dopp
$300 – Shinola Travel Kit
$200 – This is Ground Tech Dopp Kit

6. Backpack or Briefcase with Detachable Strap

Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.

Backpack Briefcase Ashley Weston 1

Backpack

$800 – This is Ground Venture Regular Backpack
$210 – Cõte & Ciel Rhine Backpack
$120 – Aer Fit Pack Backpack 

Briefcase

$990 – Frank Clegg Zip-Top Briefcase
$895 – Shinola Slim Briefcase
$325 – Uri Minkoff Pebbled Leather Fulton Briefcase 

5. Casual or Dress Watch

Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.

Casual and Dress Watch Ashley Weston

Casual Watch

$7,000 – Rolex Submariner 114060
$3,400 – Omega Speedmaster Professional Moonwatch
$375 – Orient Diver Mako USA II

Dress Watch

$12,700 – IWC Schaffhausen Portugieser Automatic
$532 – Hamilton Intra-Matic Silver Dial Leather Watch
$195 – Tissot T-Classic Tradition Silver Dial

4. White Low Top Sneakers

Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.

White Sneakers 2 Ashley Weston

$370 – Acne Studios Adrian White Leather Sneakers
$75 – Adidas Stan Smith Sneakers
$65 – Converse Jack Purcell Classic Low Top

3. Boxer Briefs

All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.

Boxer Brief Ashley Weston

$26 – Exofficio Give-N-Go Boxer Brief
$13 – H&M 3-pack Boxer Shorts
$6 – Uniqlo Supima Cotton Boxer Briefs

2. Black and Brown Casual Leather Belts

Whenever you’re wearing jeans, chinos or shorts, throw on a casual leather belt because it’ll add a visually nice touch to your outfit.

Black and Brown Casual Belts Ashley Weston

$98 – Allen Edmonds Sun River Casual Belt
$295 – Salvatore Ferragamo Reversible Leather Belt 
$18 – H&M Leather Belt

1. A Quality Wallet

The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my  article to the left for bifold, card cases, and phone wallet recommendations.

The below are only a few recommendations for bifold wallets.

Wallet Ashley Weston

$195 – Shinola Slim Bifold Leather Wallet 
$525 – Louis Vuitton Slender Wallet
$80 – Bellroy Low Down Wallet

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 Mason Leather Dopp Kit

JackSpadeMasonLeatherDoppKitAshleyWeston

 

Buy the Jack Spade Mason 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 Weston

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 Weston13

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

KillSpencerdoppfolio_34_black_1_12 Ashley 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.

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.