Gap’s Early Holiday Sale Is Here

By , a senior writer at the Strategist covering beauty, sex toys, and more. She joined the Strategist as an intern in 2018. She covers office goods, sex toys, and beauty and is also a writer for “The Approval Matrix.”

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Photo-Illustration: The Strategist; Photos: Retailers

It’s getting chilly out there, and Gap’s Holiday Kickoff Event is the perfect opportunity to stock up on sweaters, flannels, coats, and, of course, all the CashSoft. Through November 11, select winter-ready styles are up to 60 percent off; and if you shop through the app, you can get an extra 10 percent off.

Deals I personally think are the best

Gap CashSoft Crop Cardigan
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From $41
$70 now 41% off

Your new office sweater.

Gap Men's 90's Loose Jeans
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$47
$80 now 41% off

Tech writer Jordan McMahon is a fan of these jeans (that fit his “hockey butt”).

Gap Kids CashSoft Hood
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$23
$30 now 23% off

Candy-cane stripes for kids.

Women’s

Gap CashSoft Oversized Rollneck Sweater
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From $35
$90 now 61% off

An inexpensive roll-neck that’s on sale in seven colors.

Gap Modern Crewneck T-Shirt
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From $14
$30 now 53% off

“It’s a really solid, quality basic. It’s affordable. It’s reliable. It’s layerable.”

Gap Rib Scoop Tank
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$19
$25 now 24% off

Also good for layering.

Gap Vegan Suede Slouchy Tote
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$20
$70 now 71% off

The deepest discount I spotted by far.

Gap Modern Boatneck T-Shirt
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$31
$40 now 22% off

We’re all on the boatneck boat these days.

Gap CashSoft Crop Cardigan
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From $41
$70 now 41% off

Author Sable Yong is on her third CashSoft cardigan.

Gap Low Rise ’90s Loose Jeans
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From $71
$90 now 21% off

One of our favorite finds from Mall Month.

Gap Organic Stretch Cotton Hipster
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$6
$11 now 43% off

(Almost) always-on-sale hipster undies that are breathable and stretchy. Bonus: No VPL.

Gap Wool-Blend Plaid Trench Coat
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$238
$298 now 20% off

An excellent version of a classic checkered coat. This one is heavy enough to take you to winter.

Men’s

Gap Men's Straight Jeans
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From $39
$80 now 51% off

Classic straight-leg jeans.

Gap Men's Crew Socks
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From $9
$16 now 44% off

You can never have enough socks.

Gap 100% Cotton Relaxed Shaker Sweater
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$29
$60 now 52% off

A nice chunky knit.

Gap Heavyweight Denim Jacket
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$58
$98 now 41% off

Dark-wash denim is best.

Gap Men's 90's Loose Jeans
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$47
$80 now 41% off

“They fit snugly around my waist and butt while giving the rest of my legs plenty of room.”

Gap Wool-Blend Car Coat
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$148
$248 now 40% off

A heavy overcoat.

Gap CashSoft Crew Sweater
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$44
$90 now 51% off

Excellent striping this year from Gap.

Gap CashSoft Chunky Beanie
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$17
$35 now 51% off

This, too!

Kids

Gap Kids Easy Wide-Leg Drawstring Pants
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$39
$50 now 22% off

School pants that are basically PJs.

Gap Kids Square-Neck Mixed Media Dress
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$29
$60 now 52% off

A good dress for holiday parties.

Gap Kids CashSoft Oversized Fair Isle Sweater Dress
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Gap Kids CashSoft Hood
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$23
$30 now 23% off

They *probably* won’t lose this.

Gap Kids 100% Cotton Oversized Crew Sweater
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$39
$50 now 22% off

Effortlessly slouchy.

Gap Kids CashSoft Polo Sweater
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$47
$60 now 22% off

Just a bit dressier.

Gap Kids Relaxed Crop Sherpa Jacket
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$39
$98 now 60% off

They can fit a hoodie underneath.

Gap Kids Recycled Mockneck Puffer Jacket
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$58
$98 now 41% off

Another fuzzy jacket.

Gap Kids Sherpa Mitts
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$19
$40 now 53% off

Like little bear paws.

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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.

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