The Best Weekender Bags in 2023 for a Stylish Escape

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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 traveler’s arsenal. They are easy to carry around and come in all styles, colors, and materials to suit everyone’s needs.

Pack like a pro for your next wedding/business trip with a sleek garment weekender from Hook & Albert, or keep it chic in Paris with a sophisticated getaway duffle from Paravel. 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 leather 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 weekender bags that blend style and functionality into the ultimate travel companion.

For those who like to read the last page of a book first, here’s a brief overview of our picks for the best weekender bags in 2023 in a number of categories:

Best Weekender Bag in 2023: Horizn Studios SoFo Weekender

Best Weekender Bag in 2023

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 the best weekender bag 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.

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 cabin 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!

Best Weekender Bag for Men: Bennett Winch Weekender

Best Weekender Bag for Men

Key features:

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

If the perfect men’s weekend 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.

Best Weekender Bag for Women: BÉIS Weekender Bag

Best Weekender Bag for Women

Key features:

  • Separate shoe compartment
  • Water-resistant interior lining
  • Wide opening for easy access

Ladies, if what you’re seeking is a chic weekender bag with shoe compartment to take with you anywhere – from staycations and city breaks to road trips and beach escapes – you’ve found it!

Envisioned by actress Shay Mitchell, the BÉIS Weekender Bag is blissfully adaptable to your vacation needs and packed with features you’ll love, like the zip bottom compartment designed to keep your shoes and other travel essentials separate, or the smart back pocket, which converts into a trolley sleeve for easy navigation through the airport. Its spacious interior is lined with water-resistant fabric and filled with pockets, and the wide opening enables smooth access to the items inside.

The size, the looks, the price, everything about this tote just seems right!

Best Weekender for Millennials: Monos Metro Duffel

Best Weekender for Millenials

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 weekender options, but right now, none of them inspires me more to pack away and go places than this beautiful Monos bag!

Most Versatile Weekender Bag: Peak Design 35L Duffel

Versatile Weekender Bag

Key features:

  • Weatherproof recycled 600D nylon canvas shell
  • International carry-on approved
  • External side pockets for added organization

If a tough, versatile weekender bag is what your heart desires, Peak Design has the perfect product for you. Wrapped in 100% recycled 400d nylon canvas and adorned with aluminum hardware, their Travel Duffel 35L is not only good-looking but also lightweight, weatherproof, and insanely practical.

What sets this bag apart from competitors is its smart design. With a wide opening main compartment for easy packing/unpacking and just the right amount of pockets inside and out, it fits in almost any situation. Conceived with comfort and portability in mind, it comes with a melange of straps – all padded and removable, allowing you to carry it by hand, over the shoulder, and even like a backpack when you need it.

Whether used as a weekender, overnighter, gym bag, or companion carry-on for longer trips, this cabin-sized carryall makes a wonderful addition to any luggage collection.

I’ve been using this bag for a couple of years on all kinds of trips, and it’s still one of my favorite pieces of luggage. A remarkably well-made duffel with spectacular storage space!

Best Canvas Weekender Bag: Cuyana Triple Zipper Weekender

Best canvas weekender

Key features:

  • Stylish, minimalist aesthetic
  • Three separate zippered compartments for organized packing
  • Detachable leather crossbody strap

A timeless, feminine design makes Cuyana’s Triple Zipper Weekender a stylish pick for quick jaunts out of town. Its generous 3-compartment interior, along with a variety of internal/external pockets, allows you to store clothes, cosmetics, and accessories for a three-day getaway, while the delicate Soft Grey/Natural color scheme pairs well with just about anything in your wardrobe.

This chic weekender bag for women is handcrafted in Turkey from durable, textured native canvas and decked out with sleek gold metal hardware and top handles in premium Vachetta leather. A detachable leather crossbody strap facilitates carrying, and there’s also room for a few pairs of shoes in the large slip pockets inside.

Best Weekender Bag for Business Travel: Troubadour Weekender

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 weekender bag for business travel. Crafted from environmentally friendly high-spec fabric with vegetable-tanned Italian leather accents, the Troubadour Weekender makes no compromises neither on performance nor on 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, which makes it the perfect companion for the contemporary gentleman on the go. Don’t let that label frighten you, though, Troubadour Weekender is gloriously unisex, so ladies, you can enjoy it just as much.

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.

Best Vegan Leather Weekender: Db Essential Weekend Bag 40L

Best Vegan Leather Weekender

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!

Best Weekender Bag with Laptop Compartment: Away The Large Everywhere Bag

Best Designed Weekender 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 baby 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.

Best High-End Weekender Bag: RIMOWA Never Still Weekender

RIMOWA Weekender Bag

Key features:

  • Premium materials & construction
  • Separate zippered compartments
  • Rimowa’s unmistakable grooved design

Part of RIMOWA’s first-ever soft bag collection, the Never Still Weekender is refined, sophisticated, and sized just right so that you can carry it on a plane or take it on a short two-day trip.

Made in Italy using only premium materials, it sports the brand’s signature groove pattern in durable, water-repellent canvas and is accented with full-grain leather details for an extra touch of class. Inside, two spacious zipped compartments and a series of clever pockets accommodate everything needed for a short getaway or business trip, including your laptop and smartphone.

Pair all these with a removable shoulder strap, a convenient luggage sleeve, and a complimentary leather address tag, and Rimowa’s luxury weekender becomes a no-brainer investment for your stylish weekend escape.

Best Weekender Under 100: Everlane ReNew Transit Weekender

Best Weekender Under 100

Key features:

  • 100% recycled fabric with a water-resistant finish
  • Streamlined design
  • Comfortable to carry

Although designed to go into any overhead compartment, Everlane’s ReNew Transit Weekender can fit more than you might think. Made from water-resistant recycled canvas, this dapper travel tote features handy water bottle holders, a padded laptop sleeve, plus one external zip pocket for grab-and-go essentials.

The simple, practical shape and minimalist design give the weekender bag a stylish, sporty touch. Its clean interior compartment is the perfect size for about two changes of clothes, an iPad, and other travel necessities, while the combination of top handles and an adjustable shoulder strap only adds to this piece’s versatility. If you want a great weekender under $100, look no further!

Best Overnight Bag: Dagne Dover Landon Carryall Bag

Best Overnight Bag

Key features:

  • Expandable design
  • Thoughtful organizational features
  • Padded laptop sleeve

Ideal for gym trips and last-minute travel, this chic and lightweight neoprene weekender bag features a spacious main compartment along with a tone of interior and exterior pockets, pouches, and sleeves for keeping smaller items organized, as well as a removable strap so you can also wear it as a crossbody when needed.

You have 5 different sizes to choose from, but the medium Landon Carryall Bag is ideal for short trips and overnight stays, and it also conveniently fits into the overhead bin of a plane when flying. On top of that, the bag’s innovative material, available in a variety of colors, is water-resistant, hand-washable, and shock-absorbent.

Best Carry-On Weekender Bag: Paravel Grand Tour

Best Carry-On Weekender Bag

Key features:

  • Sustainable construction
  • Luxe leather accents
  • Monogrammable

Made from 17 upcycled plastic water bottles, the Grand Tour is all at once practical, elegant, and eco-friendly. Built from Paravel’s signature Ecocraft Canvas and adorned with stylish eco-certified leather detailing and premium hardware, it’s as suitable for a quick fall escape in the Catskills as it is for an epic 7-day trip to Barcelona.

At 20″ x 10″ x 11″, the sophisticated duffel is roomy enough to handle extended trips without having to check it in at the airport, and could easily compete with any item in our best carry-on bags list. Two zip interior pockets and two roomy exterior pockets will keep your small essentials organized on the go, and there’s also a removable shoulder strap for easy carrying. Each lightweight getaway bag is protected by a silicone coating to prevent stains and increase durability.

Best Weekender Bag for Longer Trips: Bellroy Weekender Plus

Bellroy Weekender Bag

Key features:

  • Clever organization
  • Large storage space
  • Weather-resistant construction

If both practicality and aesthetics are important to you, then look no further than the Weekender Plus. Meant for the modern explorer, this brilliantly functional weekend bag by Bellroy is crafted from durable, water-resistant woven fabric and finished with environmentally certified leather accents for a chic, refined look.

Its casual, harmonious design will definitely complement many looks, and the spacious interior, which includes a padded laptop sleeve and a pair of pop pockets for shoes/water bottles, will ensure you can fit everything you need for a few days away.

And the bag’s clever features don’t stop here: an organizational ‘tool belt’ facilitates access by keeping internal pockets and zips at the same height, a spacious front zip pocket holds toiletries and travel documents, while a luggage pass-through slides over the handle of your wheeled suitcase for easy mobility.

Best Weekender Bag for Adventure Travel: Filson Medium Dry Duffle

Weekender Bag for Adventure Travel

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 no doubt 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.

Best Weekender Bag with Shoe Compartment: Samsonite Quadrion 20″ Duffel

Lightweight Weekender Bag

Key features:

  • Separate shoe pocket
  • Durable, water-resistant materials
  • Lightweight

Make the most of your next spontaneous getaway with Samsonite’s latest travel duffel. Made from water-resistant 600D polyester fabric and reinforced with Kevlar fibers, the Quadrion 20″ Duffel is gloriously sturdy, lightweight, and big enough to fit a few days’ worth of outfits.

Multiple pockets and dedicated compartments help you keep clothes, shoes, and electronics organized, while its detachable padded strap adds hands-free convenience. With an integrated side shoe pocket and a price tag that won’t break the bank, this all-purpose travel bag is a real steal!

Best Weekender Backpack: Topo Designs Global Travel Bag 30L

Weekend Backpack

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 is sure to 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 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.

Best Garment Weekender Bag: Hook & Albert Women’s Fine Twill Garment Weekender

Garment Weekender for Women

Key features:

  • Integrated expandable garment section
  • Shoe pockets
  • Fold-flat design for easy storage

If you’re looking to splurge, the Women’s Fine Twill Garment Weekender from Hook & Albert is totally worth the investment.

An excellent choice for traveling professionals, this practical, lightweight bag exudes subtle luxury and sports an ingenious garment section that accommodates long dresses and a pair of shoes in perfect condition. With a sliding shoulder strap designed for carrying comfort and zip exterior pockets for storing your accessories, it can easily pass as one of the best garment bags for travel. At 20 x 13 x 9.5, the smart duffel meets all major airline carry-on requirements, and, when not in use, folds flat for easy storage.

With its durable yet refined nylon exterior and premium gold hardware accents, this piece will add a touch of class to any trip, business or pleasure.

Best Handcrafted Weekender Bag: Café Leather Robusta Weekender

Best Handcrafted Weekender Bag

Key features:

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

Modern convenience and exquisite craftmanship combine in this spectacular travel bag from Café Leather. Crafted by hand from 18Oz Twill British Millerain canvas and vegetable-tanned Specialty leather, the Robusta Weekender calls for luxurious countryside retreats and cultured city breaks alike.

From cutting to stitching, every aspect of the bag is wonderfully executed. With its timeless shape and USA-made solid brass hardware, it embodies the sense of adventure a last-minute trip requires. An adjustable/removable full leather shoulder strap and pockets for all necessities add to the functionality of the design, making it perfect to take along, whether on a quick overnight business trip or an epic multi-day adventure.

Best Leather Weekender Bag: Carl Friedrik Palissy Weekend

Best 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 are your thing, you’d be hard-pushed to find a sturdier, better-looking piece than this one.

The Sexiest Weekend Bag: O My Bag Otis Weekender

Sexiest Weekender

Key features:

  • Front compartment with magnetic closure
  • 15″ laptop compartment
  • Handcrafted from the brand’s signature eco-leather

One of the most beautiful weekenders on the list, this eco-friendly leather stunner from O My Bag hits all the right notes. Fashioned from luxurious, vegetable-tanned leather in camel, one can expect to use it for a lifetime, whether for overnight stays, weekend-long events, or spur-of-the-moment road trips.

Multiple interior storage options help jetsetters stay organized, while an exterior zipper pocket provides quick access to items on the go. Other thoughtful details include twill cotton lining and a detachable canvas shoulder strap. At L55 x W22 x H35 cm, the Otis Weekender is accepted as hand luggage for all airlines.

Best Designed Weekender Bag: Ted Baker SOPHIAZ Holdall

Designer Weekender Bag

Key features:

  • Two wheels for easy maneuvering
  • Practical front pocket
  • TSA-approved combination lock

Detailed with rose gold-toned hardware, this wheeled holdall bag from Ted Baker makes the perfect weekend accessory for globetrotters with a sense of style.

A practical and refined women’s weekender, it comes with various handles, a handy front pocket, and offers the ideal amount of storage for a city break. Its two roller wheels allow for smooth, effortless maneuverability, while the TSA-approved combination lock protects your belongings.

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