The 6 Best Madewell Bags You Can Wear Year-Round

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We’ll state the obvious: We really, (one more time for emphasis) really love Madewell. From their breezy frocks that make us want to frolic through fields of wildflowers to their impeccable line of denim (that looks fab on all body types, FYI), Madewell’s cottagecore-meets-21st century aesthetic has us wrapped around its pretty little finger. But today we’re here to shine a spotlight on their bags.

In the same way the brand’s clothing has an understated flair that seems to go with everything already in your closet, Madewell’s handbags are just as versatile. Instead of leaning into what’s trending right this second, they generally opt for vintage designs that are simple yet sophisticated, current yet classic, and durable enough to last for years. So without further ado, here are six of the best Madewell bags to shop now and wear forever.

Best Madewell Bags At A Glance:

madewell the transport tote

1. The Transport Tote

Best Overall

Chances are that you may have seen this bag slung over your coworker’s shoulder before. The unassuming style has risen its way to Madewell stardom over the years, securing its place as the brand’s best-seller—and for good reason. Crafted from buttery-soft leather that looks better with use, it comes in four, neutral colorways, like the classic, camel hue above, has interior and exterior pockets for keeping your essentials organized and can be worn either as a shoulder bag or as a crossbody, so it’s kind of like getting two handbags for the price of one.

madewell bag the sydney crossbody bag

2. The Sydney Crossbody Bag

Best Small Crossbody Bag

Presenting: Another Madewell best-seller. (Most of the bags on this list are.) A gal’s handbag collection is only as good as her best crossbody, so if you’re on the hunt for one that you'll be reaching for again and again, this baby is your best bet. It’s that Goldilocks-approved size of not being too big, nor too small, but *just right* and we especially adore how the curved shape nestles comfortably at the hip.

madewell bags the transport shoulder crossbody bag

3. The Transport Crossbody Bag

Best Medium Crossbody Bag

If boxier shapes are more your style, this fashionable, yet functionable number is a solid choice. Between the handy pockets and the zip-closure for added security, and the dual straps that allow you to wear it as a shoulder bag and a crossbody, it’s extremely versatile. And that muted, sage green color? We’re obsessed.

madewell bags the oversized shopper

4. The Oversized Shopper Bag

Best Shopper Bag

Oversized bags speak to your soul? We totally get it. This shopper-style purse checks all the boxes. It has a thick shoulder strap that won’t cut into your skin, plenty of interior space to fit everything from your laptop to your water bottle, plus a convenient exterior pocket for stowing your essentials (think: keys, mask and phone) so they’re always within reach.

madewell bags the sydney tote

5. The Sydney Tote

Best Tote Bag

Flimsy tote? Yeah, we don’t know her. This mega-bag is large and in charge, and we are fully contemplating snagging it in both colors. Similar to the styles above, this puppy is crafted from the same supple leather and features expandable side gussets, allowing you to stuff everything you need inside without altering the bag’s natural shape. Better yet, the tannery that Madewell receives its leather from received a Gold Rating from the Leather Working Group for implementing ethical and sustainable practices in sourcing the materials. Stylish as hell and eco-friendly? This tote’s got it in the bag. (Sorry, we had to.)

madewell bags transport accordion crossbody

6. The Transport Accordion Crossbody

Best Mini Bag

Just because this mini-crossbody is, well, small, doesn’t mean it skimps on functionality. Think of it as your wallet-turned-going out bag, with holding space for your cash and keys, and just enough wiggle room to stash your beloved phone. It features a zip-close compartment with two slots for your credit card and ID, and securely shuts with a collar-stud clasp. And if the paperclip chain isn’t exactly your style, good news: Madewell offers a variety of straps that you can add to your liking. (Our personal faves are this chunky, gold crossbody chain and this adjustable, rainbow-striped option).

purewow author

Commerce Editor

Anna Smutny covered a range of beats, from fashion and beauty verticals to home decor (and everything else in between) for PureWow from 2021-2022. With a background in wedding and...