Madewell Prime Day Deals
I’ve shopped at Madewell since I graduated college over a decade ago, so when the best Madewell Prime Day deals dropped, I paid attention. In my 20s, you could’ve dressed my avatar in a floral wrap dress from the brand—and honestly, not much has changed. It’s still the store I shop at most for its mix of high-quality professional and casual pieces. The brand nails wardrobe essentials with structure: jeans in wide-ranging sizes and cuts, plus polished workwear for women, shoes, and dresses that keep up with fashion trends without feeling like they’re trying too hard. I never pass up a Madewell sale, especially one this good. Right now, styles I wear on repeat are up to 50% off (my go-to work bag, the Essential Bucket Tote, is currently 25% off). These are serious, worthwhile discounts, but you’ll want to move fast. Once sizes are gone, you’re out of luck. To save you time, I’ve rounded up my (and Glamour editors’) favorite Madewell Amazon Prime Day clothing sales to shop now. Go, go, go!
Best Madewell jeans deals
Madewell translates denim trends in a timeless way, and some of its best fashion deals right now are on jeans—like 20% off the Madewell baggy jeans that convinced Glamour deputy editor Anna Moeslin to finally try the barrel-leg cut—plus straight-leg and petite jean fits that never go out of rotation.
Best Madewell clothing deals
Beyond denim, October Prime Day brings Madewell markdowns on just about everything—flowy midi and maxidresses, a Western-inspired denim jacket, cozy sweaters and cardigans, button-downs, loungewear, and soft T-shirts you’ll wear on repeat.
Best Madewell accessories deals
A few of us at Glamour (myself included) own Madewell’s slouchy suede Shopper Tote—and it’s marked down almost $70 for Prime Day, along with many of the brand’s other accessories, including shoulder bags, crossbody bags, belts, scarves, jewelry, and sunglasses.
Best Madewell shoe deals
A good chunk of my shoe shelf is devoted to Madewell—the selection is classic yet wide-ranging. Right now you’ll find some excellent Prime Day Madewell shoe markdowns on Amazon, including on the Greta Ballet Flats (25% off), which I wear to work every week. They go with everything—wide-leg jeans, dresses, leggings, you name it. If you’ve had your eye on any of the brand’s other footwear like its sneakers or on-trend boat shoes or suede loafers, now’s the moment to grab them before sizes slip away.

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