A Complete Guide to Madewell Bags

(Some affiliate links used in post.)

Hey friends!
You asked, so here it is…a Madewell bag-off, if you will!  (This post is NOT sponsored, FYI…I just love these things, ha! 😉)  Over the last six-ish years, I’ve either saved my pennies and collected or been hubby-gifted for birthday or anniversary this line of bags from Madewell, and I absolutely love their timeless design, classic coolness and the English Saddle color that make them an effortless and stylish addition to any outfit!  Below I’ll give you the rundown of what makes each bag such a great investment piece if you were wanting the opinion of a Madewell addict first hand. 😉


1 – The Transport Tote

The simple leather bag that started it all for me.  😍  If there had to be a bag that was the mascot of Madewell, it would be this: The Transport Tote.  Who would have thought a simple design similar to a grocery sack would be so popular and so replicated, but ’tis true!  Were I pressed to choose just one bag from the line up to keep, it would be The Transport Tote.  With two 8inch straps and a 13x14in body, it holds all the things (I used this instead of a diaper bag through many babies), and it is classically simple and unassuming…meaning it goes with all the things, too. 😉  There’s one inner pocket to hold keys or phone, and then I like to fill mine with smaller zippered bags to make things easy to find, like gum or lipgloss, etc.  This bag ‘o mine has taken a beating over the last six or seven years of hard use, but that only adds to it’s character and worn-in charm.




2 – Zip Top Transport Caryall

If you’re looking for a hands-free option, look no further than the Zip Top Caryall with it’s mommin-friendly crossbody strap.  HOLLER!  🙌🏼  This bag is a bit smaller than the Transport, and it’s so dang handy when you need your hands free and clear for baby-wrangling. 😉  The zipper top is also nice for keeping all the things in place whilst in the midst of said wrangling.  Still large enough to hold all the things without being too big, and I find myself frequently grateful for that adjustable crossbody strap [HERE] while I’m out mommin’ it up with my four girlies!



3 – The Transport Weekender

This is the Mama Bear of my Madewell bag collection, and I love grabbing it for a weekend away or to carry onto the airplane when I travel.  It’s just as chic and timeless as the other two bags in their Transport line, but the Weekender is able to carry that much more!  This one is definitely an investment (well, they all are…that’s why I wanted to write this post – to help dissect the line in case you were saving your pennies like I did!), but it’s timeless shape and color (plus another crossbody strap, woohoo!) make it a, well, timeless addition to your luggage.  It zips closed and has a three interior pockets plus handles and crossbody strap.  It’s just the right size for a weekend away, for packing toiletries for a longer stay or to use as a carry-on when flying!



4 – Drawstring Transport/Bucket Tote

This style is one of the newer bags I’ve purchased, and I loved this spin on the classic 70’s and 80’s bucket bag.  With a drawstring top, interior pocket, one (or two depending on which one you buy) and that beloved crossbody strap, this medium sized pretty adds texture and an unexpected shape and design to outfits!  The one pictured here is the Lafayette Bucket Bag but is currently sold out; however Madewell also sells a similarly designed option called the Drawstring Transport.  Loving this one for fall!



5 – Juniper Vachetta Shoulder Bag

The smallest of my Madewell bags was a gift from my hubby (along with the weekender ❤️), and while it’s currently sold out, I loved having a smaller shoulder bag option like this that still goes with all the things.  I’ll leave the link [HERE] in case it comes back in stock!  Love this little cutie!

Well, there ya go!  You asked, and I am always happy to chat about my favorite line of bags that I turn to year after year, season after season.  Other bags come and go, but I honestly find myself reaching for these classic, timeless beauts over and above anything else I’ve tried.  I’m drawn to the color, the cut, the shape…all the things!  Hopefully this fun little run down was helpful to you if you’ve ever considered a Madewell bag or would like to add one to your Christmas list this year. 😉



  1. Melanie Wiebe

    October 25th, 2018 at 5:51 pm

    Thanks! What a beautiful collection! 😍😍 I’ve been waiting for this post!

  2. Melissa

    October 26th, 2018 at 8:54 am

    I am in ❤️❤️❤️ with the drawstring tote! Question tho, do they ever go on sale??

  3. Erin

    October 26th, 2018 at 9:46 am

    On sale today code “ITSALOOK”

  4. Lindsay

    October 26th, 2018 at 11:02 am

    Great info! I have been thinking about purchasing a Madewell bag for some time. This helps me make my decision.

  5. Cyndie Workman

    December 31st, 2018 at 6:50 pm

    Just found your site, love your content! Been on the fence about a Madewell bag but concerned that they’re not lined. Does the inside bleed onto items you have in it?

  6. Lisa

    March 28th, 2019 at 8:36 am

    Lovely thank you for sharing this information. My husband and I just became debt free following the Dave Ramsey plan and I have learned how to save and love it. We are saving for a home/retirement although we gotta work at least 10 more years before the latter. I’m considering all things that will work with living small and stretching dollars. I love the capsule idea although I’m still working outside the hom so my wardrobe has to encompass a little more at this time. Thank you sooo much for sharing. . . it’s fun and informative to all ages/stages!

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