It’s Your Last Chance for Cheap Leset — October Prime Day Ends Tonight
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October Prime Day is here, and we’re updating this story hourly. To find the best deals in every category, follow all of our October Prime Day coverage.
Today is the last day of Amazon’s two-day October Prime Day, or Prime Big Deal Days — prices officially go up tonight at 3 a.m. ET. (It’s a shorter event than July Prime Day, a four-day sales extravaganza this year.) Now’s the time to get everything from the latest AirPods or Ceremonia heat protectant on sale. I’ve learned from covering Prime Day for years at the Strategist: It’s always better to get while the getting’s good.
And as with previous Prime Days, I’m rounding up the best Prime Day fashion deals. If you know where to look, it’s a worth-it shopping experience. The best deals remain in the Shopbop storefront, where brands that don’t go on sale often, like Leset or Loeffler Randall, get marked down. But you’ll find name brands such as Madewell, Gap, and Lands’ End marked down for upwards of 30 percent (sometimes for more than half off) throughout the megaretailer’s site. Below are the best October Prime Day fashion deals this year. Be sure to check back as I’ll be updating this guide with more deals regularly. If you’re looking for more of our Prime Day coverage, our deals editor rounded up the best discounts across all categories (with her absolutely top deals here). And sign up to receive the Strategist’s Deal Freaks Daily newsletter for our more exclusive sales coverage.
Deals I personally think are the best
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A version of the Strategist’s official “boyfriend” sweater.
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The next time Leset will be near this cheap is Black Friday.
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The underwear Joanna Goddard can’t live without.
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For people-watching (without anyone knowing you’re people-watching).
Best Women’s Deals
Women’s clothes
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Gap Factory Fitted Cami
Enjoy your single-digit singlet.
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Here’s something to layer later.
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Consider it your going-out tank.
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The V-neck edition of the T-shirt all the fashion people love.
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Gap’s Big Shirts are mightier, heartier, and weightier than Old Navy’s button-ups.
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Not a mock-neck sweatshirt, a high V-neck sweatshirt.
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Your new favorite long underwear.
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Rather sportif, if I do say so myself.
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Rah-rah!
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Not a turtleneck, but a high-enough mockneck.
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Lands’ End Jersey Knit Turtleneck
This turtleneck is between J.Crew’s Tissue Turtleneck and Uniqlo’s Heattech in weight.
Read more:The 9 Very Best Black Turtlenecks
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Maybe the cheapest Leset pointelle goes for.
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Leset Pointelle Classic Cardigan
It’s less than that Cou Cou cardigan now.
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This is a version of the 100 percent cotton oversize knit that keeps a few of us warm. “I can’t think of a cold-ish week when I haven’t pulled it out,” says our writer Tembe Denton-Hurst.
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Gap Cashsoft V-Neck Pullover Sweater
Strategist writer Brenley Goertzen, senior editor Jen Trolio, and New York deputy editor Alexis Swerdloff all wear Gap’s cashmerelike CashSoft.
Read more: Bury Me in Gap’s CashSoft
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To deal with the heat of a prewar radiator.
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Get your toasty cashmere early.
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Have a Gap-pant fall.
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Really great stripes.
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From personal experience: Donni’s poplin feels like a crisp top sheet.
Read more:I Tried All the Cotton-Poplin, Barrel-Legged, Drawstring Carpenter Pants I Could
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Gap ’90s Low-Rise Loose Jeans
Don’t worry, they’re “not low-rise, not high-rise, just under a mid-rise,” says Saloon founder Julia Harrison.
Read more: What’s Everyone Buying at Gap Right Now?
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These are similar to jeans that turned creative strategist Carrie Carrollo into a “total Gap convert.”
Read more:What Wide-Leg Jeans Is Everyone Wearing These Days?
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Our longtime best-overall women’s jeans, a favorite of Bird founder Jennifer Mankins and former Madewell creative director Joyce Lee.
Read more: I Asked Tasteful People About the Best Jeans Under $150
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Levi’s Ribcage Full Length
Our “Goldilocks of jeans,” available in full length (instead of standard ankle).
Read more: I Designed the Levi’s Ribcage Jeans
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Levi’s 318 Shaping Wide-Leg Jeans
Producer Mbiye Kasonga credits them with getting her back into jeans: “They’re categorized as ‘shaping’ jeans, so they have more give.”
Read more:What Wide-Leg Jeans Is Everyone Wearing These Days?
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The 94 is equal parts baggy and wide (an excellent ratio).
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Can you believe they’re not jeans?
Read more: All of My Friends Have These Trompe l’Oeil Sweatpant Jeans
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The Amazon Coat that’s gone down in Strategist history.
Read more: The Unlikely Tale of a $140 Amazon Coat That’s Taken Over the Upper East Side
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Levi’s Short Cotton Barn Jacket
On my mind: the barn-jacket campaign.
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By the same maker as our Best in Class (less-expensive) raincoat.
Read more:The 9 Very Best Women’s Raincoats
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Upgrade your nighttime routine.
Read more: The 12 Very Best Women’s Pajamas
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The “unicorn of undergarments,” at a Nordstrom Anniversary sale price.
Read more:The 16 Very Best Bras
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“The plain cotton Elance leaves pretty much everything to the imagination,” writes former editor Margaret Rhodes. “But that’s part of the Elance’s magic. You don’t wear these undergarments — they wear you. More exactly, they swaddle you.”
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Our Best in Class bikini — which we first heard about from Cup of Jo’s Joanna Goddard (who heard about it from Laurel Pantin of Earl Earl).
Women’s Shoes and Accessories
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Madewell The Greta Ballet Flats
Our senior kitchen and dining writer, Emma Wartzman, wore these mary janes all over SXSW.
Read more:The Flats Report
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The friulane, slipper to Italian gondoliers.
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Madewell The Mylie Ballet Flat
Consider a high-vamp flat, the mock-neck of shoes.
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Merrell Jungle Moc Mountaineering Boot
“I once regarded them as sexless, but now see them as a direct portal to the erotic,” says comedian Kate Berlant of Jungle Mocs.
Read more:Kate Berlant’s Merrells
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All the comfort of Crocs — but they’re nicer-looking.
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Hunter Play Short Rain Boot
Hunters are made for puddle-jumping.
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Walkable ankle boots.
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UGG Elea Slip-on
The late, great André Leon Talley once said, “Once you put on an UGG, you never turn back.”
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Crocs Brooklyn Low Wedge Sandals
Spend future summers in the Crocs writer Bella Druckman says are easy to clean: “Even if they get dirty, they won’t stay that way for long.”
Read more:Kork-Ease, Rothy’s, Camper: This Year’s Sandal Report
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’Tis the season of black tights.
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Le Specs Outta Love Sunglasses
These approximate the Selima Optique Aldos Carolyn Bessette Kennedy wore.
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Ray-Bans that aren’t Wayfarers.
Read more: Everyone Is Suddenly Wearing Ray-Bans Again
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Well, the name of this belt is apt.
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No friend will be able to correctly guess what you paid for it.
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It’s not balaclava weather just yet.
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Be Team Lands’ End Tote (over Team Boat and Tote).
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Lands’ End Open Canvas Tote
Or the open-top Lands’ End Tote offers easier access to your keys, lip balm, etc.
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Bogg Bag Original Large Tote
Ready yourself for a tropical vacation next summer.
Read more:The 12 Best Beach Bags
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“To quote Tom Wambsgans, [it’s] absolutely ludicrously capacious,” says our contributor Katie Stone. Her “personal capacity record” includes a laptop, a swimsuit, a sauna hat, chargers, a toiletry bag, lip balm, hand cream, a wallet, a pill case, and a water bottle.
Best Men’s Deals
Men’s Clothes
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“For a brand that invented the polo shirt 93 years ago, it’s still the best one,” says menswear writer Leon Hedgepeth of Lacoste’s L.12.12 Pique Polo.
Read more:My Hunt for a Short-Sleeved Navy Polo That Really Fits
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Lands’ End Long Sleeve Rugby
That’s one smart-looking rugby.
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Help regulate your internal temperature.
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Let go of your old holey sweatshirt.
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Under the right circumstances, it’s a jacket as well as a quarter-zip.
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The grown-up equivalent of a teenager’s favorite flannel.
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We’d like to be buried in CashSoft.
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Naadam’s cashmere has “a light-to-mid-weight feel, making it perfect for layering.”
Read more:The Very Best Men’s Cashmere Sweaters
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This doesn’t have just any gauge, it has a fine gauge.
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Not French mime–y in the slightest.
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Take a well-earned break from chinos.
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Our former menswear columnist Chris Black says 501’s are “perfect for every occasion.”
Read more:The Very Best Men’s Jeans
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There’s extra room in the 550’s compared to the 501’s.
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Gap Factory Vintage Soft Short
Your new post-workout-running-errands shorts.
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Levi’s Sherpa Trucker
Better (at least in fall) than a Levi’s trucker is a Levi’s trucker with a sherpa lining.
Men’s Shoes & Accessories
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For the pickleball court — and beyond.
Read more:The Reebok C 85 Is the Only Shoe You Should Be Seen in Playing Pickleball
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Sperry Classic CVO
Plain white Sperrys for any occasion.
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Optional: Add a Boat and Tote.
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Clarks made its first Wallabee in 1968.
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Semi-formal Jungle Mocs.
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Quarter remains the best sock length.
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Guaranteed warmth between the ears.
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Your laptop will be safe in here: “The top zipper has a strip of nylon fabric to prevent your laptop from getting scratched as you take it in and out of your bag,” says our tech writer, Jordan McMahon.
Read more:The Best Backpack Is Also a Tote
Best Kids’ Deals
Kids’ Clothes
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Quite possibly the cutest thing I’ve found this Prime Day.
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No more brr-ing.
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Everyone goes through a T. rex phase.
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The Children’s Place Baby and Toddler Girls’ Medium Weight Wind-Resistant Puffer Jacket
Stand out in a playground of black puffers.
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The Children’s Place Leggings
For cartwheels, hopscotching, and other gym-class activities.
Kids’ Shoes & Accessories
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Merrell Jungle Moc Leather Kids
The baby of the Jungle Mocs above.
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Kid-approved Crocs — senior writer Lauren Ro’s son Solomon wears them.
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Fully prevent wet socks.
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Obligatory Fuggs before their first UGGs.
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Try the bunny-ears method — without adult supervision.
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Let’s say it together: aw!
More Prime Day Deals
- There Are (Still) Some Really Good LEGO Deals
- Don’t Wait, the 83 Best Prime Day Toy Deals End Tonight
- 120 Prime Day Deals on Strategist-Approved Things End Tonight
- 19 of Our Favorite Vacuums Are on Sale for October Prime Day
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.
