Reviewing Madewell Transport Bags

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Madewell Transport Bags Review

If I’m guilty of one thing, it’s being an outfit repeater. More specifically, a bag repeater. If I find a bag I like, I’ll keep wearing the same one over and over again until you’d think I didn’t have any other bag. Part of it is practicality - if it works, don’t fix it - and part of it is laziness - it’s annoying to have to migrate your stuff into a new bag every day.

One set of bags that have been on serious repeat, especially here on the blog are my Madewell Transport line bags. The Transport bags by Madewell are a blogger favorite and I have the privilege of owning three different ones. I know many people have these already but there are also many more who are thinking of purchasing them too so today I’m here to do a quick review of the ones I have that I wear all the time.

Madewell Small Transport Crossbody

Madewell Small Transport crossbody bag


  • Top button closure

  • Big front pocket, no inside pocket

  • Two straps - a top handle and detachable shoulder straps

  • 7 3/4"H x 7 3/4"W x 2 5/8"D

  • Retails at $128

The Good, the Bad, and the Ugly

This was the very first bag from the Transport series I ever bought and I loved it. Still love it, in fact. I believe this particular burgundy color is discontinued but I also love the soft brown color and it also comes in black. I wanted the burgundy because it was such a rich color that looks good with all outfits. My color palette has been more neutral as of late and this bag is a great pop of color without being too loud. It holds a surprisingly large amount of stuff. The strap is not too long (something I do have trouble with at times due to my petite height) and when worn as a crossbody, it hits me slightly below my hips. It’s a great size for every day. It does scratch somewhat easily though and you can see on my bag all the scuff marks. However, since it’s leather, I kind of enjoy that weathered look so I don’t mind it. Just something to keep in mind if you don’t like easily scratched leather bags.

Madewell Transport Rucksack

Madewell Transport Rucksack


  • Outside pocket with button flap closure

  • Collar stud closure

  • 14 1/2"H x 10 1/2"W x 7"D

  • Retails at $198

The Good, the Bad, and The Ugly

I never thought of myself as a backpack person but they’ve really grown on me the last few years. I loved the look of a chic leather backpack (it helps me shred my Jansport-wearing days of middle school). It’s perfect to wear to work or even play because it’s easy to dress up and down. I definitely feel sporty wearing it but, in a chic and feminine way, if that makes sense? Definitely my style.

The kicker of wearing a leather backpack though? The weight. It’s definitely on the heavier side and I tend to carry heavy things in it because that’s the point of a backpack, right? Carrying bigger things in a bag that’ll evenly distribute the weight. But with the bag itself being heavy, it can definitely get tiring carrying it all.

Madewell Transport Tote

Madewell The Transport Tote


  • Simple design with no outside pockets

  • No closure whatsover - just raw leather

  • Small pocket on the inside

  • 13 3/4"H x 14"W x 6 1/4"D.

  • Retails at $168

The Good, The Bad, and The Ugly

Ahh, the classic Transport tote - the bag that originated it all! The Transport tote is about as simple and no-frills as you can get. There are no pockets, no designs, no crazy details. Like all the other Madewell leather bags, you do have the option of getting it monogrammed (my aunt sent me this bag with the monogram but I’m personally not a big monogrammer), but otherwise, it’s classic. I love the slouchy leather and the raw edges. However I do wish there were more options for organizing the contents. Everything in the bag sort of gets mashed together. I also wish there were some way to close it. It’s fine where I live but I can imagine if I traveled with it, I’d be a bit more aware of pickpockets. However, it’s a great classic work bag and it fits everything I could ever need in a day.