Gap, Merrell, Rothy’s: All the Best October Prime Day Fashion Deals
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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 marks the first day of October Prime Day, or Amazon’s Prime Big Deal Days, a two-day sales event running from 3:01 a.m. ET on October 6 to 2:59 a.m. ET on October 7. You’ll notice that it’s shorter than July Prime Day, which was a four-day sales extravaganza this year. As October Prime Day has half the amount of days, you’ll want to shop sooner rather than later. Prices can go up before the end of the day, as I’ve learned from covering Prime Day for years at the Strategist.
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 Rothy’s 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. And if you’re looking for more of our sales coverage, sign up to receive the Strategist’s Deal Freaks Daily newsletter.
Deals I personally think are the best
Women’s Deals
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Here’s something to layer later.
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Some three-packs of gum cost more than each tank.
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From personal experience: Gap’s Big Shirts are mightier, heartier, and weightier than Old Navy’s button-ups.
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Your new favorite long underwear.
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Maybe the cheapest Leset pointelle goes for.
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It’s 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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Have a Gap-pant fall.
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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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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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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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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 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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There’s no break-in period needed before it forms to your feet “in the least Birkenstock way possible,” says contributor Erika Veurink.
Read more: “I Walked 15,000 Steps a Day Around Florence in These Mary Janes”
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Our senior kitchen and dining writer, Emma Wartzman, wore these mary janes all over SXSW.
Read more:The Flats Report
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Hunters for a light-rain kind of day.
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“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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In the same family as the Encores Sandy Liang dedicated a haiku to.
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The late great André Leon Talley once said, “Once you put on an UGG, you never turn back.”
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Walkable ankle boots.
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Plan to spend next summer in Mary-Kate Olsen’s Tevas.
Read more: “Mary-Kate Olsen and I Both Own a Pair of Rather Nice-Looking Tevas”
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Swap your regular brown suede belt for a leopard calf-hair one.
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It’s not balaclava weather just yet.
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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, swimsuit, sauna hat, chargers, toiletry bag, lip balm, hand cream, wallet, pill case, and water bottle.
Men’s Deals
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Your Columbia fleece replacement.
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Proudly wear the crocodile logo.
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Take a well-earned break from chinos.
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Levi’s original zip-fly style since 1967.
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There’s extra room in the 550s compared to the 501s.
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Not boxers, not briefs: boxer-briefs.
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Optional: Add a Boat and Tote.
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Semi-formal Jungle Mocs.
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Very The Row–y — and not a whole lot.
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Guaranteed warmth between the ears.
Kids’ Deals
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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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For cartwheels, hopscotching, and other gym-class activities.
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Better than the GAP font is mascot Brannan Bear.
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The baby of the Jungle Mocs above.
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Obligatory Fuggs before their first Uggs.
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Try the bunny-ears method — without adult supervision.
More Prime Day Deals
- An Under-$50 Brio Train Set and and More Prime Day Toy Deals
- Everything We’ve Written About That’s on Sale for October Prime Day
- Hydro Flasks, Headphones, LEGO, and More: Prime Day Deals That Make Great Gifts
- A Buy-It-for-Life Vacuum Is 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.
