The Best Men’s Weekender Bags of 2019

Whether you’re taking a weekend getaway or packing up for a shorter business trip, a stylish, functional weekender bag is the perfect travel companion. We’ve discussed some of our favorite weekender-style bags before, but these bags are so useful and versatile that we decided it was time for an update. All of these bags meet carry-on requirements and are ideal for 1-3 days of travel. Here are our picks for the best weekender bags of 2019.

Check out all our picks below plus a few extra bags that we added for good measure!

 

Stuart & Lau -$385

A truly excellent bag, we love the mix of waterproof nylon and full grain leather, as well as the simple, lined interior and clean design. An added bonus, this bag comes in multiple sharp color options and also comes with a matching, full-grain leather strap. It may seem like a small detail but the two exterior pockets on each end are a really handy design detail that gives you some extra storage flexibility. The navy and tan colorway we tested was great, but we also really like the olive and black combo.

 

Herschel – $90

We’re big fans of Hershel’s backpacks, briefcases, and wallets, so it makes sense that their weekender bag would be excellent as well. This bag boasts a very nice price point that belies it’s sturdy, high-quality construction and materials. It’s constructed with heavy-duty nylon and has an integrated shoe compartment that we thought was a nice feature. While we preferred the basic, monochromatic black and grey colors, the huge range of colors and patterns is a nice bonus if you prefer more colorful options.

 

Everlane – $98

As with all things Everlane, this bag has a great price point and super simple, classy design. In our previous weekender video, we chose this one as well, but it had a rubber bottom. In this newer version, they’ve done away with that and added metal feet instead, which we feel is a downgrade. But overall, it’s still a great bag at a great price.

 

Combatant Gentlemen – $110

We loved the price point and mix of leather and canvas with the shoe handy shoe compartments and this bag is a really excellent value. The bag has a unique garment bag design to it but in the end, we weren’t a fan of this aspect because it could potentially affect the clothes you normally put in a garment bag as they can get smashed on the sides and bottom. But, other than this small part, this bag was really great.

 

Frost River – $215

The Frost River bag is made in the USA and boasts a great mix of affordability and quality.  It’s constructed with heavy-duty materials that will age beautifully and last a long time. The leather accents are very nice and the hardware is sturdy. The top zipper design opens up very wide to make packing easier and the exterior pockets are perfect for stashing books, magazines or an iPad, both nice design touches.

 

Filson – $395

Another made in the USA, heritage brand, Filson builds extremely durable, handsome bags that will literally last you a lifetime.  If you favor the more rugged, woodsy look, this is the bag for you.  It’s constructed of very sturdy canvas, outstanding leather accents, and strong hardware.  It has a very large capacity and features a beautiful all-leather shoulder strap. This bag takes some time to break in but will only get better over time.

 

Want Les Essentials – $450

This stylish weekender bag boasts a sleek, monochromatic design that we really loved. There’s minimal branding and it features very nice cotton canvas accented with Italian leather details. We loved that the entire base was leather, a very nice touch. While the shoulder strap wasn’t all leather, overall this bag is very nice and has exceptional design.

 

Billykirk – $550

Another outstanding American-made bag, Billykirk is known for their leather goods and excellent quality.  This handsome bag is made from heavy waxed canvas and very nice leather accents (including an all-leather shoulder strap!) that will age beautifully. The style is clean and simple but with a bit of a rugged vibe that’s not too over-the-top. It’s really a great mix of modern classic styles. It comes in two great colorways but we especially love the all-black version, it’s really sharp.  This bag also comes in smaller and larger versions, so if you’re looking for more or less space but love the looks you’ve got some options here.

 

Frank Clegg – $925

Dorian has owned this bag personally for 4 years now and it looks brand new. This bag has it all: clean, classic design, buttery soft tumbled leather that just gets softer with age, an all-leather shoulder strap, lined interior and no metal feet on the bottom. Plus the design features just the right amount of structure to it. It’s a pleasure to own and use this bag, it’s the best of the best.

POTW: Leather Weekender Bag

We see a ton of bags, some good ones and plenty of bad ones, and finding a good-looking AND well-priced leather weekender bag can be super tough.  We recently got a chance to check out one of the weekender bags from Beckett Simonon and we were so impressed we had to make it our Pick of the Week!

The bag features excellent leather quality, a solid build and a nice set of features, all at a great price.  We loved the tan color but it also comes in a few other colorways.  Make sure to check out the links below for all the options!

      

Tan Weekender Bag

 

      

Black Weekender Bag

 

      

Oxblood Weekender Bag

 

      

Their Other Collections

 

Dorian’s Outfit

Topman Shirt

Barton Perreira Glasses

Nvidia Grenchen Chronomaster (Vintage)

Watch Strap

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