14 Best Weekender Bags That Are Cute and Incredibly Roomy

Creatively designed, this versatile weekender opens flat, much like a rolling suitcase. Once it's open, you'll get access to multiple zippered compartments, including breathable mesh pockets, to keep all of your belongings—enough for a few days—safe and secure. The exterior features both a detachable padded shoulder strap and top handles; plus, the whole thing secures to another suitcase, thanks to the trolley sleeve. And to top it all off, the whole thing is water-resistant.

• Pros: Water-resistant, roomy interior with multiple compartments; three ways to carry it
• Cons: Expensive, heavy
• Dimensions: 20.9 x 11.8 x 9.4 in.
• Weight: 3.3 lbs.
• Material: Nylon, leather

I can barely handle my clean clothes touching any dirty laundry I accumulate along the way, let alone my shoes. That's why a bag like this one is so appealing—it has an entirely separate zippered shoe compartment to keep everything where it should be: away from each other. It also comes equipped with nice-to-haves like a laptop pouch, a zippered exterior pocket to keep essentials in reach, and a trolley sleeve. And despite its utilitarian design and budget-friendly price tag, this bag is surprisingly sophisticated. I'm a sucker for anything with gold hardware.

• Pros: Waterproof shoe compartment; multiple ways to carry; affordable
• Cons: A bit bulky, especially since it's a bit stiff.
• Dimensions: 17.3 x 8.4 x 14.5 in.
• Weight: 2.4 lbs.
• Material: Nylon, faux leather

Looking for something smarter than your average bag? This sleek leather one is it. I can't tell you how soft the cow leather feels in person—it truly feels like a luxury item. Plus, it wears well, developing a slight patina over time, which is something I happen to love. It's not the roomiest bag I've ever owned, but there's definitely enough space inside for a night or two if you pack creatively including a pair of shoes or a laptop. It also has functional compartments for items like a water bottle or charger.

• Pros: Soft leather construction, multiple compartments inside
• Cons: Not as roomy as other options, expensive.
• Dimensions: 13⅜ x 22¾ x 7¼ in.
• Weight: Not listed
• Material: Cow leather

I didn't go to a single sleepover during high school or a single trip during college without my Vera Bradley tote attached to my hip. And although my tastes have outgrown the chintzy floral patterns I once relied on, the practicality of the brand's bag is not lost on me—which is why I'm thrilled to see solids and more muted patterns in today's lineup of the classic. The bag is incredibly roomy and the zipper may as well have superpowers, because mine never once failed to stretch past a mountain of clothes over the course of at least 10 years.

• Pros: Tons of colors and patterns, exceptionally roomy interior; two ways to carry
• Cons: Not water-resistant
• Dimensions: 26 x 13 x 13 in.
• Weight: Not listed
• Material: Cotton

It's no surprise that Herschel, known for its sturdy canvas backpacks, makes a great weekender too. The traditional oval-shaped duffel, complete with its zippered top, is well equipped to hold it all. It has a sizable interior that includes a mesh pocket. Plus, there's a separate zippered pocket on the outside for quick access to small essentials. I've always loved the leather-accented options, but it's hard to resist all of the fun colors on offer, like this calming lilac, which is easy to spot in a crowd.

• Pros: Comes in a wide range of colors; canvas is easy to clean; two ways to carry
• Cons: Strap tends to dig in when bag is full.
• Dimensions: 20 x 8.75 x 8.75 in.
• Weight: 2 lbs.
• Material: Canvas

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A looker? Not necessarily, but this giant workhorse holds literally everything, says commerce director Brie Schwartz. “It has taken me around the world (well, around the country) and back,” she says “Though it's spacious, it squishes down to fit in overhead compartments, and the padded backpack straps make it comfortable to haul on your back, leaving your hands free for a roller bag if you're an overpacker like me.”

• Pros: Very roomy, highly durable; can be worn as a backpack
• Cons: Not the most attractive option
• Dimensions: 26.7 x 15.7 x 11.8 in.
• Weight: 2 lbs., 9.1 oz.
• Material: Polyester

It may look like nothing more than a cute designer bag, but senior commerce editor Talia Abbas says this extra-large tote is worth a second glance—despite the fact that it doesn't have a zippered top or much more than a small inside zippered pocket and two outer side pockets. “It could carry all my clothes and shoe bags…and probably a small child,” she jokes. But really, when you're trying to fit as much as you can into one bag, that's exactly what you want to hear. At only 17 ounces, it's also nice and light, giving you more wiggle room to stuff it with other things and still not struggle to carry the bag. “It fits everything and weighs nothing,” Abbas adds. “The colorful mesh doesn't really dirty, and the canvas straps are durable but also surprisingly comfortable. It's doubled as my gym bag at home and beach bag on longer trips too.”

• Pros: Lightweight; water-resistant nylon, ample room inside; folds flat to make it even more packable
• Cons: Expensive, no zippered top, only one interior pocket.
• Dimensions: 17 x 12.5 x 9 in.
• Weight: 17 oz.
• Material: Canvas

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You can spot this duffel bag from a mile away—a great thing if you end up checking your bag. Of course, it also comes in more muted shades like olive, gray, and black, if that's your thing. Either way, this high-quality travel bag has a roomy interior complete with a removable zip pouch, plus an exterior pocket, as well as interior zip and mesh pockets and a lightly padded laptop sleeve that can fit up to a 16-inch model. Carry it with the handles or add the cross-body strap—it's entirely up to you.

• Pros: Two ways to carry; neoprene material is easy to wipe clean; comes in a variety of colors.
• Cons: Expensive, on the heavier side, not machine-washable.
• Dimensions: 16.5 x 9 x 11 in.
• Weight: 2.9 lbs.
• Material: Neoprene

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“Much like the person reading this, I was on the hunt for the perfect weekender bag,” says associate beauty editor Danielle Sinay. “And in the midst of all my googling, a sponsored Instagram ad for the Béis Weekender got the best of me. And I am so glad it did!” This gorgeous large bag fits everything you could need—and possibly more—for a few days away, with multiple organizational pockets and pouches to help you pack smarter. No more shoving all your personal items and hoping for the best when you go through the TSA. “Now I actually find my things upon arrival—and I’m a heavy packer (think: every beauty product you could ever imagine).” Sinay's favorite features are the interior laptop sleeve, key hook, adjustable straps, and easily accessible bottom compartment designated for shoes, toiletries, and whatever else you want to keep separate. The zipper on the back also functions as a trolley sleeve, so you you can pop the bag onto your carry-on roller and/or luggage handle without a second thought (or back pain).

• Pros: Water-repellant, large size; laptop sleeve
• Cons: Heavy
• Dimensions: 15½ x 18½ x 10 in.
• Weight: 3.8 lbs.
• Material: Polyester, faux leather

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This weekender isn't a cult favorite just because it's supercute; it's also cleverly designed to help you make the most of limited space. The zip-top canvas bag opens wide to reveal enough space for one to two days’ worth of clothes, a toiletry kit, and—bonus!—a laptop up to 15 inches. The eco-friendly material, made of recycled water bottles, repels both water and stains and is exceptionally easy to wipe clean if something does spoil its beauty. The personalization element is just the icing on the cake. “I used to have the tote version of this bag and loved it!” Abbas says. “It wasn't big enough for weekend trips, which is why I have my eye on this bigger style. I like the contrast of the black leather trim against the gray canvas, and the fact that you can monogram the bags with more than just your initials; there are some really cute emoji too!”

• Pros: Can be personalized; stain-repellant; trolley sleeve
• Cons: Expensive; longer strap sold separately.
• Dimensions: 15 x 15 x 8 in.
• Weight: 2.4 lbs.
• Material: Canvas

This minimalist waterproof bag is the perfect size for a day trip or weekend getaway—even one with a less-than-optimal weather forecast. “Despite being soft and unfussy, it’s handsome enough to make even my schlubbiest airport outfit look put together,” says commerce writer Jake Smith. And while some people may gravitate toward bags with multiple compartments for organization, Smith says he loves the fact that this one has only a single main compartment. “There’s less room to lose all my odds and ends.” The bag includes a detachable shoulder strap, but Smith suggests carrying it by the handles. “You’ll look expensive.”

• Pros: Waterproof, less expensive than other options; removable shoulder strap,
• Cons: On the smaller side
• Dimensions: 9.1 x 15.7 x 7.9 in.
• Weight: 22.6 oz.
• Material: Polyester

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A dream is a wish come true, right? There's no doubt all eyes will be on you with this medium duffel in hand. It has the ever-recognizable Gucci pattern and red and green stripes, yes, but it's so much more than a pretty piece of luggage. This carryall has enough space for a full weekend's worth of gear, and comes equipped with a matching luggage tag and a lock with a key holder to keep your goods safe.

• Pros: High style, roomy interior; comes with accessories like a luggage tag and lock
• Cons: Relatively heavy when filled, expensive
• Dimensions: 17.5 x 10.5 x 9.5 in.
• Weight: 3.7 lbs.
• Material: Leather, nylon