These Are the Best Men’s Weekender Bags of the Year

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The weekender bag is a practical, versatile piece of luggage designed for short trips. Large enough to fit a few days’ worth of clothing, yet compact enough to stow in the overhead compartment, these smart accessories deserve a special place in any men’s arsenal.

Pack like a pro for your next business trip with a smart, minimalist-looking weekender from Troubadour, or keep it classy in Italy with a sophisticated handmade leather carry from Carl Friedrik. For those who want to rough it in style, there’s hardly a better option than Filson’s kick-ass dry duffel, while for everyone else, there’s always a sublimely versatile canvas travel bag that screams both cozy countryside affair and luxurious city escape.

Wherever your whirlwind trip may take you, make sure you stand out with one of these handsome men’s weekender bags that blend style and functionality into the ultimate travel companion.

Bennett Winch Weekender

Men's Weekender Bag

Key features:

  • Separate waterproof shoe compartment
  • Padded laptop sleeve
  • Military-grade cotton webbing handles & shoulder strap

If the perfect men’s weekender bag exists, it has to be one dreamed up in a bar and sketched on the back of a napkin – case in point, Bennett Winch’s signature carry, which strikes the perfect balance between ruggedness and refinement.

Handmade in England using 24oz British-dyed waterproof cotton canvas and finished with full-grain leather handles and base, The Weekender is as much a fashion statement as it is a practical piece of luggage. Ideal for a 2 to 5-day getaway, it’s packed with clever details like a padded laptop sleeve and two waterproof compartments for keeping your footwear and gym essentials separated from the clean stuff.

Db Essential Weekend Bag 40L

Vegan leather weekender bag for men

Key features:

  • Db’s patented Hook-Up System
  • Accessible front pocket
  • Carry-on approved

If you’re looking for a vegan leather weekender bag that fuses streamlined aesthetics with technical touches, then this innovative duffel from Db is the one for you. Made from premium quality PU leather, it can easily hold all of your weekend essentials in the spacious main compartment and has a classic silhouette that will go well with just about anything.

The detachable shoulder strap allows for breezy, comfortable transportation, while a handful of pockets keep contents organized and within reach. No matter the outfit, season, or destination, you can never go wrong with this contemporary weekender for men!

Horizn Studios SoFo Weekender

Best weekender bag for men

Key features:

  • Lightweight & durable water-sealed cotton canvas
  • Luggage pass-through
  • Interior and exterior pockets

Clean lines, classic form, and impeccable construction make this luggage piece one of the best weekender bags in 2023. With a water-resistant waxed canvas outer shell and ample room for outfit changes throughout the trip, Horizn Studios’ SoFo Weekender is ready for any adventure without compromising your look. While not specifically a men’s weekender bag, it’s an ideal pick for spontaneous guys with insatiable wanderlust, flexible travel plans, and a sense of style.

Inspired by (and named after) Stockholm’s hippest and most creative neighborhood, it boasts a simple, savvy design with separate pockets inside and out, including one that allows you to secure it to larger Horizn Studios rolling luggage. The padded carrying handles and removable adjustable shoulder strap make this lightweight weekender bag easy to transport even over long distances.

I recently took the SoFo Weekender on a quick 2-night getaway to Lisbon and had more than enough room to fit everything. Not only that, but the bag is as beautiful as it is practical, which makes it a joy to pack and carry around. My favorite feature? It’s lightweight. For a heavy packer like myself, there’s nothing more annoying than toting around a bag that’s already heavy before you put anything in it. Can’t wait to use it as a carry-on on my next flight!

Troubadour Weekender

Best men's weekender bag for business travel

Key features:

  • Padded laptop compartment
  • Waterproof fabric
  • Clean, refined look

Exceptional functionality, innovative materials, and clean, contemporary aesthetics come together to create the best men’s weekender bag for business travel. Crafted from environmentally friendly high-spec fabric with vegetable-tanned Italian leather accents, the Troubadour Weekender makes no compromises on performance, quality, or design. In fact, no other bag on this list manages to draw such a fine line between elegance and performance, formality and casualness, strength and finesse.

The waterproof canvas keeps your gear safe from the elements, multiple pockets provide smart storage for your work and tech essentials, while its modern, minimalist looks are adaptable to all styles and travel scenarios, making it the perfect companion for the contemporary gentleman on the go.

And yes, the bag is carry-on friendly and fitted out with all the modern bells and whistles, including a trolly sleeve that doubles as a pocket when zipped up, an internal laptop compartment, and a detachable non-slip shoulder strap for hands-free carrying.

Carl Friedrik Palissy Weekend

Vachetta leather weekender bag

Key features:

  • Handmade in Italy from premium Vachetta leather
  • Curved profile for maximum packing space
  • Personalisation options

Carry your short trip essentials in style with the stunning Palissy Weekend by Carl Friedrik. This bag gives you the best of both worlds: timeless elegance fused into a modern shape.

Handcrafted from premium Italian Vachetta leather in a chic cognac hue, it makes an inspired accessory for a weekend away in the English countryside, but it’s sure to steal looks wherever you go.

The interior is lined with soft nylon canvas and equipped with pockets for your valuables, and there’s also a removable shoulder strap for added versatility. The quality and craftsmanship are outstanding, and, if leather weekender bags for men are what you’re after, you’d be hard-pushed to find a sturdier, better-looking piece than this one.

Topo Designs Global Travel Bag 30L

Carry-on weekender bag

Key features:

  • Stellar internal organization
  • 3-way carry options
  • Clam-shell opening for easy packing

Whether you’re off on a business trip or a city break, the Global Travel Bag 30 L will fit all your traveling needs. Its versatility alone makes this Topo Designs pick an excellent carry-on suitcase for men, but add in multiple carrying options and an abundance of organizational features, and you’ve got yourself one of the best men’s weekender bags on the market.

Crafted from durable, recycled nylon, this practical backpack is small enough to pass as a carry-on, yet large enough to hold all your on-the-move essentials. Accompanying its roomy main compartment are a wealth of internal/external pockets for keeping your stuff in order, as well as an external, easy-access laptop sleeve.

Samsonite Armage II Expandable Duffel

Expandable duffel from Samsonite

Key features:

  • Expandable construction
  • Durable, recycled materials
  • Great organization

Make the most of your next spontaneous getaway with this expandable duffel from Samsonite. Made from durable, recycled polyester fabric and reinforced with abrasion-resistant YKK zippers, the Armage II is gloriously sturdy, well-organized, and big enough to fit a few days’ worth of outfits.

Multiple pockets, zippered storage bags, and dedicated compartments help you keep clothes, accessories, and electronics in place, while its luggage sleeve and detachable strap add hands-free convenience. With two levels of expansion and a price tag that won’t break the bank, this all-purpose men’s travel bag is a real steal! It also has a business-like appearance that makes it great for work trips and formal occasions.

Monos Metro Duffel

Monos Metro Duffel

Key features:

  • Detachable Metro Kit pouch
  • 15″ laptop sleeve
  • Built-in trolley sleeve

One of the most good-looking weekenders on this list, the Monos Metro Duffel has us dreaming of relaxing winery getaways and stylish escapades to small-town gems.

It’s compact but roomy, strong but delicate, smart enough for business travel, yet stylish enough for European city breaks. Made from buttery vegan leather, it’s also good for the Earth, water & scratch-resistant, and endlessly versatile.

A 15” laptop compartment, a built-in trolley sleeve that converts into a pocket, and an assortment of inner pockets are here to fulfill all your organizational needs. And as if that wasn’t enough, each duffel comes with the collection’s signature Metro Classic Kit, an insanely convenient matching pouch that snaps on and off the bag magnetically so that it can be easily removed, used separately, and even attached to the equally chic Metro Backpack.

There’s no doubt the market is replete with wonderful men’s weekender options, but right now, none of them inspire us more to pack away and go places than this beautiful Monos bag!

Tecovas Weekender

Waxed canvas weekender

Key Features

  • Heritage quality
  • Built to last a lifetime
  • Surprisingly spacious

This Texan brand may be known for its leather cowboy boots, but they’re also making a statement with this sturdy waxed canvas duffel, which combines modern convenience with exquisite craftsmanship. Crafted from a robust duck cotton cloth treated with Martexin wax, the Tecovas Weekender calls for rugged adventures and cultured city breaks alike.

From cutting to stitching, every aspect of the bag is wonderfully executed. With its timeless shape, solid brass hardware, and Presidio leather details, it embodies the sense of adventure a last-minute trip requires. An adjustable/removable shoulder strap and pockets for all necessities add to the functionality of the design, making it one of the best travel bags for men looking to carry their gear in style.

Filson Medium Dry Duffle

Adventure duffel

Key features:

  • Fully waterproof
  • Abrasion-resistant polyurethane coating
  • Roll top with hook-and-loop tab closure

Created with outdoor expeditions in mind, Filson’s Medium Dry Duffle is undoubtedly one of the best adventure duffels on the market. Extremely durable, weatherproof, abrasion-resistant, and easy to carry, this rugged cylinder travel bag is in a league of its own. You can wear it on your shoulder, tie it to the back of your truck, and even drag it down the road.

The 54-liter volume provides ideal storage for any wild weekend adventure you may embark on, while the watertight roll-and-cinch closure means your contents remain dry and protected even when the bag is fully submerged.

Away The Large Everywhere Bag

Everywhere Bag

Key features:

  • Sleek, water-resistant nylon exterior
  • Smart interior organization system
  • Packs like a suitcase

Perfectly sized for a short getaway, Away’s Large Everywhere Bag pairs form and function beautifully. Crafted from water-resistant nylon, it features an exterior padded 15” laptop sleeve and comes in colors that complement its beautiful classic look with tasteful leather accents.

Though similar to the smaller Everywhere Bag, this new bag stands out for its updated design, with a clever clamshell opening that enables efficient suitcase-style packing and easy access to the main compartment. A detachable shoulder strap paired with long top handles adds flexibility in carrying, while a thoughtful internal organization system, complete with a water bottle pocket and detachable key clip, keeps travel necessities in order. And if you thought it couldn’t get better, the bag is also carry-on size and designed to secure to any Away suitcase for a smooth roll through the airport terminal.