Photo-Illustration: The Strategist; Photo: Retailer
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.
From
$31
$80
now
61% off
From
$12
$20
now
41% off
$124
$295
now
58% off
$14
$30
now
53% off
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 mention Crown Affair founder Dianna Cohen, Bird’s Jennifer Mankins, and former Madewell creative director Joyce Lee).
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.
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.
The 501s in short form. These are the Platonic ideal of a cutoff, especially for the perfectly frayed hem.
A wisp of a tank that’s not too thin.
A ribbed tank that’s not too tight.
And a ballet tee that’s not too basic.
I’m eyeing this breezy minidress with fluttery sleeves.
A little black dress with cut-outs at the neckline and hem.
And a little white dress that ties in front.
A T-shirt dress for all seasons: easy on its own in the summer, and easy to layer in the winter.
The offseason is often the best time to buy a sweater — and here’s a handsome one from Vince for hundreds of dollars off.
These biker shorts are majorly marked down and have been a huge hit with Strategist readers.
Pair the shorts with this cropped tank for a sleek set.
If you’re feeling inspired to pick up a tennis racket after watching Challengers, you’ll need a skirt to serve in.
Strategist writer Brenley Goertzen is an avid runner, and these are her go-to leggings — they even come with a built-in running belt.
Shorts for running laps or running errands.
A solid one-piece with supportive straps for more than 60 percent off.
Calvin Klein is one of the most reliable names in underwear; I’d recommend buying its three-packs in bulk.
While you’re at it, get the matching bralette in multiples, too.
A delightfully dowdy nightgown that’s currently half the price of a Salter House one.
A work tote that’s big enough to schlep a laptop with a top zipper to keep all your stuff secure.
This shoulder bag has a polished look, if you’re in need of a more formal version of your Baggu Crescent.
We’ve been hearing that Vera Bradley is poised for a comeback — this plaid duffel would make a good weekender for fall trips.
The weaving on this Bembien shoulder bag makes it look much more expensive than it is.
These sculptural hoops look like Bottega Veneta’s for less than $10.
A statement-making bow earring to level up your earscape.
To zhuzh a messy updo.
I’ve been searching for a sun hat that doesn’t cost a fortune, and this pretty pink one might be it.
For more than 50 percent off, you can’t go wrong with a simple belt.
Shimmery statement socks to glam up your ankles.
Take a cue from Bella Hadid: Small sunnies are in.
Oval might be the most popular sunglasses shape right now, and these are very much a nod to Carolyn Bessette’s.
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.”
“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.
Trade your Dickies chinos for these cooler Carhartt cargos.
Stylist Law Roach asks for a new pair of these sweatpants every Christmas.
Playwright Matthew Gasda wears Brooks Brothers’s Non-Iron Oxford button-downs to his “living room” plays, paired with a tweed jacket and corduroys.
The shirt of choice for “sporty coastal elites.”
For an even preppier polo, here’s a logo’d one from Brooks Brothers.
If Sambas and Crocs had a baby, these slides would be it.
There’s a good level of sportiness to these sneakers without going full tennis pro.
Boat shoes for yachting … or just renting a sailboat for the day.
Dr. Martens’s hard-wearing Chelsea boots aren’t often on sale, so I imagine the sizes on these will go quickly.
These slippers remind me of the kind in fancier hotels, but more plush.
The hexagon-shaped frames on these sunglasses are a little less obvious than the aviator-style Ray-Ban is famous for.
Keep this warm wool scarf for yourself, or give it as a gift for the holidays.
These button-shaped cuff links will make a French-cuff shirt look more bespoke.
This might be the daddest of dad caps (in a good way).
I’m ready to call these the cutest shoes you’ll see in the sale.
Three pairs of shorts for less than the price of one.
Strategist writer Liza Corsillo tipped me off to these adorable tanks from Gap — I like the flower-power-peace-sign one the most.
A striped tee that’s perfect for Picture Day.
If your kid wears a uniform to school, stock up.
For kids who aren’t quite ready to tie their own laces, but are already off to the races.
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.