Still not convinced that Gap is, in fact, so back? Allow the Gap Cyber Monday sale to make the case for us, courtesy of a staggering 50% off the brand’s entire site.
For the last few years, Gap’s long-awaited comeback has yielded some of the most wearable, least-pretentious menswear on the market—and right now nearly all of it is marked down like the good ol’ days. Which means there’s a mouth-watering array of archival bangers and contemporary workhorses flying off the line like comfort food at your local diner.
Keep scrolling to see what we’re eyeing immediately below, or head on over to Gap itself and get shopping.
Want more savings intel? Start with our guide to the best Cyber Monday clothing deals, then make moves to GQ’s all-in-one master list of every Cyber Week deal that matters.
The Best Gap Cyber Monday Deals to Buy Now
The Planet-Friendly Puffer
Gap Recycled Heavyweight Puffer Jacket
See the deal
The Rough-and-Rugged Flannel
Gap Organic Cotton Relaxed Flannel Shirt
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The Soft-and-Slouchy Pants
Gap 365 Wool-Blend Relaxed Trousers
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The Neck-Saving Scarf
Gap CashSoft Cable-Knit Scarf
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The Slinky Sweater
Gap Fuzzy Relaxed Crop Cardigan Sweater
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Outerwear Deals
Gap
Wool-Blend Bomber Jacket
Bombs—and we can’t reiterate this enough—away
Gap
Relaxed Corduroy Jacket
There’s a lot of ways you can get lost in the sauce with corduroy. When its done poorly it can be straight up bad. But we promise this jacket won’t lead you astray.
Gap
French Terry Chore Jacket
You can (and should) wear this as a chore coat for whatever fall weather we left, but once coziness becomes more of a priority it’s going to be a dynamite couch cardigan, too.
Gap
Denim Lined Zip Chore Jacket
You don’t have to ditch the chore coat when winter hits.
Gap
Wool-Blend Car Coat
A beautiful wool coat for under $100? This is just getting silly now.
Gap
Recycled Heavyweight Puffer Jacket
This perfect, earthy brown is the kind of perfectly-chosen puffer color you never normally see at these prices.
Shirting Deals
Gap
Organic Cotton Relaxed Flannel Shirt
A good flannel is pretty much always worth the price, even if it gets steep—this one just so happens to be as good as a bunch of steep ones and under $30.
Gap
Oxford Shirt
It’s unclear if anyone is keeping track of these things, but navy oxfords might be the most underrated (and one of the most versatile) of the classic oxford colors.
Gap
Relaxed Straight Hem Oxford Shirt
If you’re trying to tone down a button-up, the quickest way is to flatten that hem.
Gap
Corduroy Shirt Jacket
Flannel gets all the shine when it comes to cold-weather wovens, but corduroy does nearly everything it’s cotton compatriot does and also boasts some welcome texture.
Sweats and Sweater Deals
Gap
Extra Heavyweight French Terry Zip Hoodie
The humble zip hoodie deserves your respect and most importantly it deserves a spot in your wardrobe rotation.
Gap
Merino Wool-Blend Polo Sweater
Relaxed enough to wear with some faded jeans, refined enough to compliment some slacks and machine washable in case you end up wearing it too much.
Gap
Fuzzy Relaxed Crop Cardigan Sweater
For anyone with a cardigan-sized hole in their life, this one will fill that hole with zero air gaps.
Gap
Wool-Blend Zip Cardigan Sweater
Never underestimate the power of a two-way zipper.
Pants Deals
Gap
Heavyweight Relaxed Straight Jeans
If the relaxed or baggy cut denim isn’t your thing, you can always trust in the good ‘ol straight fit.
Gap
Canvas ’90s Loose Carpenters Pants
If you don’t beat these up, you’re doing it wrong.
Gap
90s Loose Jeans
One of the best cuts in the catalog is currently under $50.
Gap
Relaxed Straight Jeans
The wide-leg trend isn’t forever, or for everyone. A relaxed straight, however…
Accessory Deals
Gap
CashSoft Beanie
Top off your fit with one of the best affordable beanies money can buy.
Gap
CashSoft Scarf
The Wu-Tang Clan always gives sage advice: “protect ya neck.”
Gap
CashSoft Cable-Knit Scarf
Once you become a scarf guy you’ll wonder how you ever weren’t a scarf guy.
Gap
Drawcord Hood
This is one of those items you throw on when the wind chill starts to dip into the single digits.
Gap
Leather Gloves
Once again, a pair of gloves will do wonders for your outdoor mood in the coming months.
Gap
Braided Leather Belt
Considering we’re entering prime time Big Meal territory, a highly-adjustable belt could be useful.
Gap Cyber Week FAQ
What are the best things to buy at Gap?
The best things to buy at Gap? Start with the hits. The brand has been on a heater lately, mining its deep archive for all-star classics while dialing in modern silhouettes and workwear staples. Outerwear (especially the lighter layers), pants, shirts, sweaters, and sweats are all strong plays—especially if you haven’t checked in for a while.
This year in the US, Black Friday is on Friday, November 28, a day after Thanksgiving. While that’s the official date, many retailers roll out deals throughout November. You can expect the biggest discounts to happen between Thanksgiving and Cyber Monday, but be on the look out for retailers to launch sales early.
Cyber Monday lands on December 1 this year, the Monday after Thanksgiving. Most brands keep the deals rolling through the week—but don’t bank on it.
