The 76 Best Prime Day Fashion Deals (That End Tonight)
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Today is the last day of Amazon’s two-day Prime Day sale, a.k.a. the Strategist equivalent to the Super Bowl. Everyone on our staff has been obsessively tracking the best deals we can find on everything from vacuums and mattresses to skin care and a particularly fancy bidet. As the site’s style writer, I’ve been digging through all the fashion deals, and featuring only the deepest discounts.
I’ve covered Prime Day for five years in a row now, and my golden rule is to look for deals that are at least 20 percent off (the only exceptions are the items that truly never go on sale). There were lots of Levi’s jeans and Madewell accessories marked down for the first day of Prime Day, and I’m expecting stock to start disappearing quickly as the last-minute rush sets in for Day Two. The Shopbop and Zappos sections of the sale also have a number of highlights — including the Natori Feathers bra (the “unicorn of undergarments”) and Wolford shimmer socks. Below, you’ll find all those and more; check back often, as I’ll be updating this guide until Prime Day is over. And to see all of our absolute favorite deals across all product categories, read our guide to the very best Prime Day deals, according to the Strategist writers.
The Deals I Personally Think Are the Best
I’m excited to see Levi’s Wedgies — our best-in-class jeans — on sale for the cheapest I’ve seen them in a while. One find I’m eyeing for myself is this thin-but-not-too-thin tank from Madewell that will be infinitely layerable. Then there’s an incredible deal on a pair of See by Chloé flats, which were originally $295 but are now $124; I like that they don’t look too precious, as ballet flats sometimes do. And finally, some short-shorts from Free People, for exercising or otherwise, are just $14.
Best Women’s Clothing Deals
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Levi’s Wedgie Straight Jeans
The Wedgies just might be the jeans we’ve written about most on the Strategist. They’re a well-made, well-fitting favorite of mine (not to mentionCrown Affair founder Dianna Cohen, Bird’s Jennifer Mankins, and former Madewell creative director Joyce Lee).
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Back in 2019, we dubbed the Ribcages the “Goldilocks of jeans.” Even now, I still hear about them all the time. They fit just like the pair you hope to find while sifting through a thrift store — high-waisted, with a leg-lengthening straight cut.
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The 501s are the original true-blue jean, and Levi’s has kept the fit and button fly intact since 1873. Because there’s no stretch in the denim, stylist Karla Welch recommends “wearing them, and wearing them, and wearing them, and wearing them” until they’re broken in.
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Levi’s 501 Original Shorts
The 501s in short form. These are the Platonic ideal of a cutoff, especially for the perfectly frayed hem.
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Madewell Whisper Cotton V-Neck Tank
A wisp of a tank that’s not too thin.
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And a ballet tee that’s not too basic.
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Contrasting stripes make for a fun button-down.
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Gap Flutter Mini Dress
I’m eyeing this breezy minidress with fluttery sleeves.
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A little black dress with cut-outs at the neckline and hem.
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And a little white dress that ties in front.
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Kule Tee Dress
A T-shirt dress for all seasons: easy on its own in the summer, and easy to layer in the winter.
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The offseason is often the best time to buy a sweater — and here’s a handsome one from Vince for hundreds of dollars off.
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These biker shorts are majorly marked down and have been a huge hit with Strategist readers.
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Pair the shorts with this cropped tank for a sleek set.
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If you’re feeling inspired to pick up a tennis racket after watching Challengers, you’ll need a skirt to serve in.
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Strategist writer Brenley Goertzen is an avid runner, and these are her go-to leggings — they even come with a built-in running belt.
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Shorts for running laps or running errands.
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A solid one-piece with supportive straps for more than 60 percent off.
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A nice-looking cover-up.
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Calvin Klein is one of the most reliable names in underwear; I’d recommend buying its three-packs in bulk.
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While you’re at it, get the matching bralette in multiples, too.
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Natori Feathers Contour Plunge Bra
Writer Molly Lamoureux describes Natori’s Feathers bra as “the unicorn of undergarments.”
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A delightfully dowdy nightgown that’s currently half the price of a Salter House one.
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Cup of Jo’s Joanna Goddard included Eberjey’s Gisele pajamas on her list of things she can’t live without — twice.
Best Women’s Shoes Deals
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A few weeks ago, I went searching for the best sandals on sale. Surprisingly, these Dr. Martens are still marked down to around the same price. So really, don’t dillydally.
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New York deputy editor Alexis Swerdloff caught a “very fashionable person” wearing these platform Crocs over the weekend.
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“I just think jelly everything is going to be everywhere this summer,” The Love List newsletter editor Jess Graves told me. This pair is a good way to try the trend.
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Slides that are easy to put on and go with everything.
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A dupe for Hermès’s Oran sandals for as cheap as I’ve seen them so far this summer.
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Veja Urca Sneakers
The “quiet cult” around Vejas is still going strong — the shoes are among the best white sneakers.
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You’ll often see Catbird’s Leigh Plessner around town in a pair of Havaianas.
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Because no one likes wet feet.
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I love the laces on these See by Chloé flats.
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A sharp-looking pair of pointed flats. Plus, they’re conveniently machine-washable.
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Party heels you can actually dance in.
Best Women’s Accessories Deals
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A work tote that’s big enough to schlep a laptop with a top zipper to keep all your stuff secure.
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We’ve been hearing that Vera Bradley is poised for a comeback — this plaid duffel would make a good weekender for fall trips.
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Bembien Marni Bag
The weaving on this Bembien shoulder bag makes it look much more expensive than it is.
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Apsvo Chunky Gold Hoop Earrings
These sculptural hoops look like Bottega Veneta’s for less than $10.
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A statement-making bow earring to level up your earscape.
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I’ve been searching for a sun hat that doesn’t cost a fortune, and this pretty pink one might be it.
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For more than 50 percent off, you can’t go wrong with a simple belt.
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Shimmery statement socks to glam up your ankles.
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Take a cue from Bella Hadid: Small sunnies are in.
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Oval might be the most popular sunglasses shape right now, and these are very much a nod to Carolyn Bessette’s.
Best Men’s Clothing Deals
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The 501s are also the gold standard when it comes to jeans for men. Our menswear columnist Chris Black describes them as “perfect for every occasion.”
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Levi’s 511 Slim-Fit Jeans
“The Levi’s 511 is to slim-fit jeans what the 501 is to straight-leg jeans: a standard-bearer,” writes Strategist contributor Charles McFarlane. With the slimmer silhouette comes some stretch to make these super-comfortable.
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Trade your Dickies chinos for these cooler Carhartt cargos.
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Stylist Law Roach asks for a new pair of these sweatpants every Christmas.
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Playwright Matthew Gasda wears Brooks Brothers’s Non-Iron Oxford button-downs to his “living room” plays, paired with a tweed jacket and corduroys.
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The shirt of choice for “sporty coastal elites.”
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For an even preppier polo, here’s a logo’d one from Brooks Brothers.
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A classic jean jacket for the fall.
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If you’re a “boxers over briefs” person, these Polo ones are nice.
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If Sambas and Crocs had a baby, these slides would be it.
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Veja Volley Sneakers
There’s a good level of sportiness to these sneakers without going full tennis pro.
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Sperry Top-Sider Leeward 2 Eye Boat Shoe
Boat shoes for yachting … or just renting a sailboat for the day.
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Dr. Martens’s hard-wearing Chelsea boots aren’t often on sale, so I imagine the sizes on these will go quickly.
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These slippers remind me of the kind in fancier hotels, but more plush.
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The hexagon-shaped frames on these sunglasses are a little less obvious than the aviator-style Ray-Ban is famous for.
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Keep this warm wool scarf for yourself, or give it as a gift for the holidays.
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These button-shaped cuff links will make a French-cuff shirt look more bespoke.
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This might be the daddest of dad caps (in a good way).
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I’m ready to call these the cutest shoes you’ll see in the sale.
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Three pairs of shorts for less than the price of one.
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Strategist writer Liza Corsillo tipped me off to these adorable tanks from Gap — I like the flower-power-peace-sign one the most.
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A striped tee that’s perfect for Picture Day.
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If your kid wears a uniform to school, stock up.
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For kids who aren’t quite ready to tie their own laces but are already off to the races.
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A summer staple that can handle both the playground and the splash pad.
The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.
