Ask the Edit: Stylish Weekender Bags

Oct 24, 2017

Hi Belle,

I’m looking for a decent sized stylish weekender bag for shorter trips.  My L.L. Bean boat tote from college isn’t cutting it anymore. I would love a bag with pockets or compartments so it doesn’t become a giant black hole.

Thanks! Katie

Having a weekender for a quick trip is an essential.  No one wants to drag their roller-board around for a change of clothes or two.  A simple leather bag is a classic.  This is the bag I use.

The Cuyana Le Sud Travel Bag ($375) is the perfect weekender.  It’s just big enough without being too big.  Sometimes “weekenders” are so large, you wonder who needs that much for a short trip.

The bag has a detachable shoulder strap, and the regular straps have a generous drop.  You can also expand the size of the bag using the buckles on the sides.  The inside has a side pocket wide enough for a 15″ laptop.  It also has two interior zip pockets.

This is a very luxurious bag, that would make a wonderful gift.  You can also monogram it (up to 8 characters) for a personal touch.

Looking for something less expensive? Matt & Nat make wonderful bags, they have a large one and a medium size one.  Sole Society also has a faux-leather oversize weekender and a cool travel satchel.  For a bargain option, this H&M bag is a nice choice.

Prefer a canvas bag?  This Madewell Transport weekender has a unisex style.  This Everlane twill weekender is a popular choice.  Their nylon weekender would also make an excellent gym bag.

Do you have a favorite weekender?  And how many days can you pack for?  I can manage a Friday to Sunday, but that’s about all.  I have just resigned myself to the fact I will never be one of those girls who can pack light for any occasion.

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  1. Melissa says:

    The Lo and Sons weekender is great! They have several different sizes and shapes, tons of colors, and have a zippered section in the bottom. This bag has done a 4 day trip to Iceland in Freezing December, and an 8 day trip to Iceland and Denmark in a warmish December. Lo and Sons also runs frequents sales, and you can get one for under $100.

  2. Katherine says:

    I love my Longchamp Le Pliage Expandable Travel bag. It’s weekend sized and super lightweight, and then can expand and double in size – great for trip purchases or the general difficulties of getting everything packed as tightly at the end of the trip as it was at the beginning.

    • Sara K says:

      I use this one too. It’s a great weekender and I often use it as my carry on luggage. I do wish it had pockets, but I end up using Eagle Creek compression bags to organize all my stuff.

  3. Cait says:

    I bought the previous version of this weekender about 5 years ago when I desperately needed something to pack in for a last minute trip. I expected it to last through my trip and not much else, but now I still use it several times a month. I can fit 4 days of summer clothes or 3 days of winter clothes. It’s easy to stuff into an overhead bin but also fits under most airplane seats depending on how full you pack it. I’m a heavy weekend traveler, and I tend to bash my luggage around a bit, so I’ve been pleasantly surprised by how well this bag has held up!
    https://www.amazon.com/Classic-Weekender-Overnight-Duffel-Leather/dp/B06XW5F5BG/ref=sr_1_5_mc?s=apparel&rps=1&ie=UTF8&qid=1508856157&sr=1-5&keywords=canvas%2Bweekender&th=1

  4. Nora says:

    The Henri Bendel West 57th Weekend Duffle is amazing. It’s absolutely gorgeous and I get so many compliments on it, every time I use it. I love that is is structured so it holds its shape. The inside has a large zippered pocket, then 4 open pocket (2 of which are on the ends, so I throw shoes in there sometimes.) It also comes with a lock, if that is something that is important to you. It’s a bit pricey, but a lot of times Henri Bendel has discounts for how much you spend.

  5. Mo says:

    I can pack for two weeks in a carry-on roller board, but for a weekend I need at least a Lo and Sons Catalina, which is about the same size.

    I blame running clothes and the fact I don’t go anywhere w/o my Sedu blow dryer.

  6. Lisa says:

    The Soul Society vegan weekender is a really great option for the price. I’ve had mine for a few years now and it’s really held up well zipping back and forth across the country. I always get compliments on it, and someone once asked me if it was a Coach leather duffel. Now, I don’t think the fake leather is THAT good, but it goes to show the quality for the price point. It’s on the small side, but I’ve packed for up to 5 days before.

  7. Jennifer says:

    I love Tuckernuck’s weekender “Sunshine Satchel,” which can also be monogramed. I purchased mine three years ago and still use it all the time for quick weekend jaunts and driving trips. Big enough to hold a couple days worth of clothes, plus a pair of shoes (or two!) and your hair dryer. Similar to the L.L. Bean tote, but with leather accents, handles and a shoulder strap, and a zip top. Highly recommend – mine looks as good as new.

  8. Jules says:

    I have a couple bags I enjoy from lululemon. I think technically, they are ‘gym’ bags, but once in a while they have very sleek, cute bags that look nothing like something you’d shove in a locker.

    Also, since they are gym bags, I’ve found they come with a lot of compartments, which is nice.

  9. Katie Hathaway says:

    Do you find the Cuyana to be heavy to carry when full because of the leather?

  10. MissMaple says:

    I bought a Fossil coated canvas duffel about five years back that I really like. I don’t know that they still make the same one, but the ‘Vintage Key-Per’ they have now is pretty close. It’s held up well on frequent trips on buses and in cars up and down the Eastern Seaboard and doesn’t really show any signs of wear. I can easily fit everything for a 3-4 day long weekend, but it gets a bit tight beyond that. I also like that it’s lighter than the all-leather ones.

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