prime day 2023

We Found Lots of Levi’s Under $50 — and 79 More Prime Day Fashion Deals

Photo-Illustration: The Strategist; Photo: Lewis Osborne, Retailer

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Amazon’s eighth-annual Prime Day — or days, really — is almost over. You probably know the basics by now, but here’s a quick summary: It’s a Prime-members-exclusive event (you can sign up for a free 30-day trial) with very limited-time lightning deals along with two-day-only ones. It’s become a shopping holiday of sorts, like Black Friday. Honestly, Prime Day is like our Super Bowl.

Past Prime Days have taught me that to get the best fashion discounts, you have to do a little digging. Amazon’s in-house brands — including the Drop and Amazon Essentials — almost never go on sale aside from Prime Day, when you can find them for around 20 to 30 percent off (such as a pair of strappy sandals below). There’s always a trove of markdowns on Levi’s jeans and Calvin Klein underwear (it’s time to stock up on those three-packs). But one of the greatest secrets is the Shopbop section (the high-end designer site is owned by the big-box retailer): Last year, I spotted Falke socks, Staud bags, and Loeffler Randall hats hidden away there. This year, there are markdowns on Mara Hoffman swimsuits, Kule totes, and Smythson card holders. (It also feels more curated than the Prime Day landing page.)

Below, I’ve rounded up the best Prime Day 2023 fashion deals, including Strategist favorites like Levi’s “deliriously high” Ribcage jeans and classic Hanes white T-shirts. I’ve included any bargain so good I couldn’t not mention it; all items are at least 20 percent off, unless they’re one of those products that are rarely (if ever) on sale. On the second day of Prime Day, stock usually sells out faster than the first. The best advice I have: Don’t dillydally!

That’s especially true as Prime Day winds down. Although I’m finished checking this post for the night, all of the deals below will stay live as late as 2:59 a.m. ET — just keep in mind that availability and stock can change as folks finalize their carts. Our deals editor will be back on Thursday morning with a rundown of the best post–Prime Day sales. And to make sure you don’t miss anything, why not sign up for our newsletter, too?

Women’s clothing


Our most-written-about jeans are almost 40 percent off in select washes. You won’t get an actual wedgie in them, contrary to their name.

We’ve named the Levi’s Ribcage the “Goldilocks of jeans” for its super-high rise and straight-leg shape. Strategist editor Maxine Builder predicted it would be the new Wedgie. New York deputy editor Alexis Swerdloff likes that the jeans are “stiff without being too constricting” with “just the right amount of flare.”

The 720 is among Levi’s skinniest of skinny jeans. Still, writer Diana McCorry says the style has “enough stretch to avoid that nasty tummy compression but enough shape to create a great silhouette when you stand up.”

Levi’s 501 Pieced Jeans

And these have a DIY air about them — as though you sewed two pairs of 501s together, thanks to some interesting seaming.

Levi’s 501 Original Shorts

If you’re in the market for jorts that show some leg, the cutoff version of Levi’s legendary 501s — complete with a frayed hem — is now 40 percent off.

Levi’s 501 Mid-Thigh Short

The mid-thigh version is even more deeply discounted at almost 60 percent off.

A sexy halter for festival season — or Daisy Jones cosplaying.

Levi’s Alyssa Denim Jumper

You could wear this denim dress on its own — or layer it with a T-shirt or turtleneck for something a little more grungy.

Theory Double Pleat Pant

These are similar to the pleated Vince pants that Strategist beauty writer Tembe Denton-Hurst called her best buy of 2022. Hers are $345, while Theory’s come in at $180 on sale.

LNA Martin Tee

An upgrade to a plain-white tee — with shoulder-baring cutouts.

If you’re vacationing somewhere tropical soon, this tiered tent dress can pack nicely in a suitcase (and since it’s already airy, you won’t have to mess with a steamer).

It wouldn’t be Prime Day if the famous Amazon coat — first seen on the Upper East Side in 2018 — wasn’t on sale. It’s slightly more expensive than it was during the company’s October Prime sale but nonetheless a Very Good Deal at $50 off. The faux-fur-trimmed version is discounted too.

If you must go to the office, this double-breasted blazer will look sharp through even the most boring of meetings.

As featured in the newsletter Perfectly Imperfect (hat tip to Swerdloff). These are also tag-free with more moderate coverage, so they’re a little cheekier — in a good way.

Many a model has crowed about “my Calvins,” but the brand is beloved for a reason. Rapper Junglepussy praised the undies’ “smooth finish under fitted clothing,” and emphasized that “their fabric keeps the coochie fresca.” Enough said. These are going fast in different colorways, but a set of classic black, white, and gray is still in stock (for now).

If you’re the thong type, these barely-there panties are made from a seamless microfiber. Plus there are no tags to itch or irritate.

In our guide to the best bras for small breasts, this ThirdLove bra won the title of “Best Overall.” Though I’m not small-chested myself, I was impressed with the fit of it — I didn’t have any trouble with spillage. (FYI: You’ll need to clip the on-page coupon and then a 20 percent discount will show up at checkout.)

Even after Lauren Stephens, co-founder of Dudley Stephens, stopped working in Calvin Klein’s PR department, she remained a fan of the brand. The memory foam on her favorite bra — which we’ve named the best T-shirt bra — forms to the body for a better fit.

And this strapless bra features smoothing cups that are cut slightly lower so they don’t peek out from a neckline.

Selling Sunset star Christine Quinn, a self-professed “creature of habit,” can’t live without this bralette. She recommends the matching thongs too. “They’re also so breathable, which, believe it or not, is a hard thing to find,” Quinn promises.

Pepper makes small-chest-specific bras (including AA, A, and B cups). The All You is one of the brand’s bestsellers. Strategist writer Lauren Ro likes that it keeps her natural shape: “There’s nothing worse than when your boobs just look like the cups of the bra.”

In our guide to the best wireless bras for large breasts, this True & Co. took the title of “best seamless.” Strategist contributor Brodie Lancaster considers it among her favorite work-from-home bras for its “full-coverage, long-enough-to-be-a-crop-top” cut.

This lacy little number is another bargain from True & Co. at 40 percent off.

Mara Hoffman Gabriela One-Piece

Since Barbie-mania is in full swing, this one-piece from Mara Hoffman feels of the moment. (The Baywatch–esque high-leg cut will make it a favorite for seasons to come, too.)

Mara Hoffman Gabriela One-Piece

Or this trippier print might be more to your taste.

Peixoto Ora Dress

It’s a cover-up that you could actually get away with wearing as a dress. I especially like the diamond-shaped eyelet trim.

This shirt reminds me of Ina Garten’s Hamptons uniform on Barefoot Contessa. (Note: The matching shorts are sold out at the moment.)


Spanx’s shapewear is known for smoothing without smothering. These leggings are designed with shaping support with a double-layered waistband and no center seam (read: no camel toe).

If you already own Outdoor VoicesExercise Dress in multiples, you might try the Bianca from Girlfriend Collective. It has a built-in unitard liner with a support band under the bust (so you could theoretically go braless) — and yes, there are pockets on the inside.

These Marina PJs from Sleepy Jones are similar to the Sleepy Jones set that Karlie Kloss sleeps in — her mother instilled in her the belief that “when you go to bed in matching pajamas, you sleep better.” The pajamas are made completely from cotton for the hot sleepers among us.

Women’s shoes

A strappy pair of sandals — with a not-too-high heel — for wedding season.

Mary janes can sometimes look sophomoric but not these. And the square toe keeps them fresh. (I’m a sucker for the shiny faux patent leather, too.)

Sam Edelman Lennon Mule

Sam Edelman makes one of our favorite loafers. These backless Lennons have the chunkiness the brand is known for.


The British boot brand has very few styles on sale (the boots are all over the place, price-wise). These gladiator sandals are a highlight for something edgier than a flip-flop.

These are a version of the Sorels that Strategist contributor Diksha Basu calls Marni-esque: “Over-the-top in the best way, they look a little bit Marni, a little bit Suzanne Rae for Teva.” And they’re almost 70 percent off in this coral colorway.

These color-blocked mules have a chic but manageable kitten heel.


Swedish sneaker label Tretorn “first made waves on tennis courts and at prep schools in the 1970s,” explains Nicolas Lazaro, a former community specialist at the menswear-resale platform Grailed. Pair these more than 40 percent off Rawlins3s with a polo to nod to their history.

These on-sale Crocs feature a 1.6-inch platform for a little extra boost.

UGG’s Fluffettes are a cousin of the Coquettes, which we named the best slipper for women. These have a warm wool lining and a fluffier outsole.

Women’s accessories

For a beach getaway — or (discreet) people-watching on a park bench.

Or for something more eye-catching, these Le Specs come in a banana-yellow shade.


These Burberry shades have a more muted boldness — think of them as the middle ground between the Ray-Bans and Le Specs above.


Parisian designer Sylvia Toledano is known for her bright enamel pieces — these heart-shaped hoops are decorated with a rainbow’s worth of dots.

KULE Large Strawberry Tote

One-up the standard Boat and Tote with Kule’s statement-making strawberry-emblazoned one.

A.P.C. Laure Tote

Here’s a minimalist bag for the denim nerds who take pride in breaking in their jeans from the French label.

The crocheted marigolds make this Lele Sadoughi bag too pretty to pass up — especially at over 50 percent off.

Streamline your about-to-pop wallet by downsizing to this slim card holder. (Plus, Smythson is known for its luxury leather.)

Men’s clothing

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,” explains Strategist contributor Charles McFarlane in our guide to the best jeans for men. Stylist Brandon Garr likes that he “can be a bit more daring in them” since he doesn’t have “to worry as much about the replacement cost if they get a little roughed up.”


To go for a full Canadian tuxedo.

Vince Hemp Pull-On Short

I was surprised to find these Vince pull-on shorts for half off — especially since they’re made of (usually expensive) hemp.

For a bolder take on a short-sleeved button-down, this one is printed with an abstract floral design instead of more typical stripes.

Or if you’re not a print person, here’s a short-sleeved oxford-style shirt that comes in several solid colors and a couple of windowpane patterns for those days when you’re feeling daring.

This Paul Smith button-down has a kitschy, quirky Bode vibe.

$40 for 5

Cheerleading coach Andy Cosferent (from Netflix’s Cheer) calls these trunks comfortable, praising how they stay in place.

These already cheap Champion sweats are even cheaper at the moment. The joggers have a slimmer leg than what’s traditional, making them less slouchy-looking.