Maybe you’re an everyday nurse like Diana Prince by day and a golden-lasso-wielding Wonder Woman by night. Maybe your usually-chipper-self has a dark side that appears when you feel hangry. Or maybe you’re “the quiet one” whose inner pop star comes alive with a karaoke mic in hand. Alter egos come in many different forms—and in this case, yours just might be carrying one of our ready-for-anything canvas bags. Read on to find out which one will have you switching up your usual style.


You: can’t travel anywhere without an overstuffed rolling suitcase

Your alter ego carries: the streamlined Transport Weekender

Traveling with this rugged-cool weekender, you won’t need five extra outfit options because your alter ego is a frequent flier who has the versatile vacay wardrobe that goes seamlessly from coffee to cocktails and fits easily inside a just-spacious-enough bag. As your expert-packer other half, you always answer “yes” to a spontaneous road trip. Bonus points for calling shotgun.

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Interviewing our Transport Collection (Really, Hear Us Out)


A few years ago, our design team set out to create something simple: a timeless tote so free of trendy details that you could carry it for as long as the leather would allow (aka forever). The result: our Transport Tote. Since then, we’ve added some new shapes and sizes, and while they all share the same rugged yet refined style—thanks to fine leather, minimal hardware and tonal stitching—each has its own pretty unique vibe. Allow us, or, um, them, to explain.

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#totewell: Tales of a Transport Tote



If there were a Best Supporting Actress award for wardrobe, the Transport Tote would win year after year.

Talk about breadth of character. It’s as versatile as it is ruggedly elegant, whether it’s resting contentedly in the basket of your bicycle or carrying a freshly plucked bouquet. Without a clasp or label—save the owner’s monogram—its biggest identifying mark is the very absence of one.

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According to us, all submissions to our #totewell Instagram contest are winners, but we did promise to narrow it down to three. Meet the Instagrammers who stole our hearts (figuratively and digitally).







Each of the winners will receive $1,000 Madewell gift cards (let the obsessive deliberations begin). And because we couldn’t resist, see a few more of our favorite submissions on Facebook here.

P.S. Don’t stop the #totewell love. Your pictures may still end up in our gallery on