16 Best Madewell Prime Day Deals, According to a Shopper of 10+ Years


This is the brand I buy from most—so when I say the deals are good, I mean it.
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Madewell Prime Day Deals

Best Madewell Prime Day Jeans Deal
Madewell The Balloon Jeans
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Best Madewell Prime Day Clothing Deal
Madewell Poplin Smocked Maxi Dress
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Best Madewell Prime Day Accessories Deal
Madewell Oversized Suede Shopper Tote
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Best Madewell Prime Day Shoe Deal
Madewell The Greta Ballet Flat
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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.

  • Courtesy of brand
  • Original video from Jenifer Calle testing Madewell The Balloon Jean

Madewell The Balloon Jeans

Madewell petite barrel jeans
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Madewell Petite Darted Barrel Leg Jeans

Madewell Dean Easy Straight Jeans
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Madewell Dean Easy Straight Jeans

Madewell Longline Straight Jeans
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Madewell Longline Straight Jeans

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.

Madewell Poplin Smocked Maxi Dress
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Madewell Poplin Smocked Maxi Dress

Madewell Denim Trapeze Jacket
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Madewell Denim Trapeze Jacket

Madewell Striped Ribbed-Sleeve Sweater
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Madewell Striped Ribbed-Sleeve Sweater

Madewell The Melody Scoop Back Smocked Midi Dress
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Madewell The Melody Scoop Back Smocked Midi Dress

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.

Madewell Oversized Suede Shopper Tote
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Madewell Oversized Suede Shopper Tote

Madewell Chunky Metal Leather Belt
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Madewell Chunky Metal Leather Belt

Madewell Essentials Crescent Sling Bag
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Madewell Essentials Crescent Sling Bag

Madewell Suede Essentials Slouch Hobo Bag
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Madewell Suede Essentials Slouch Hobo Bag

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.

Madewell The Jamie Boat Shoe
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Madewell The Jamie Boat Shoe

Madewell Kickoff Trainer Sneakers in Neutral Colorblock Leather
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Madewell Kickoff Trainer Sneakers in Neutral Colorblock Leather

Madewell The Greta Ballet Flat
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Madewell The Greta Ballet Flat

Madewell Dimes Kitten Heel Boots
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Madewell Dimes Kitten Heel Boots