The 12 Best Things to Buy from Gap’s Blowout VIP Sale

Welcome to Add to Cart, a (semi)regular segment that spotlights the best pieces of menswear to buy at a bargain from across the web.


You probably remember Gap (there was a “the” unofficially tacked on at some point long ago, though the brand itself always favored the simpler moniker) from back-to-school shopping trips to the mall with your long-suffering mother and her endless reserves of patience. Well, you might not be going back to, ah, anywhere at the moment, but Gap is still a force to be reckoned with this time of year. The brand can’t stop—won’t stop!—doing everything in its power to entice customers to walk through its virtual doors, often in the form of some truly eye-watering discounts.

I’m not going to lie, it’s always a little bittersweet to see prices slashed this low, even temporarily, but it’s also a welcome reminder of how much heat the retailer still stocks. In the years since those formative trips, Gap might not have stayed top of mind when it came to meeting your everyday menswear needs. But it remains a veritable American institution, the place to go if you’re looking to stock up on basics at “Um, is this correct?” prices, or not-so-basics at prices that belie how damn good the product looks.

Speaking of sweet, sweet discounts, right now the retailer happens to be taking 40% off almost everything, along with an additional 20% off that, and if you move fast, you can still get in on the action. So why not take the opportunity to get to know Gap once again? And then say sorry to your mother. I’m not sure for what, precisely, but chances are you owe her one.

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Recycled Cozy Scarf

Gap gap.com

$29.95 $16.15

Scarf season is in full effect. 

Vintage Soft Slim Sweatpants

Gap gap.com

$44.95 $24.24

The perfect pair of retro-inspired striped sweatpants…

Vintage Soft Hoodie

Gap gap.com

$44.95 $24.24

…and the perfect hoodie to pair ’em with. 

Marled Turtleneck Sweater

Gap gap.com

$45.00 $24.27

Frankly, I’m sucker for marled anything, and that’s doubly true when any sort of (very good) knitwear is involved. 

Twill Shirt Jacket

Gap gap.com

$59.95 $32.33

Wear it just like the model does here, and then prepare yourself for random strangers to ask you—from a safe distance, please—where you copped your jacket. 

Denim Western Shirt

Gap gap.com

$59.95 $32.33

Here’s a little-known fact: it’s only after Labor Day that the opportunities to wear white really get interesting. 

Oversized Sweater

Gap gap.com

$69.95 $37.73

See what I’m saying?

Denim Worker Shirt

Gap gap.com

$79.95 $43.12

A shirt that reads as all-American as baseball, apple pie, and, well, Gap itself. 

Ribbed Shawl Cardigan

Gap gap.com

$79.95 $43.12

Bundle me up, daddy. 

Reversible Fleece Jacket

Gap gap.com

$98.00 $52.86

Fleece life 4eva. 

Workforce Collection Utility Jacket

Gap gap.com

$98.00 $52.86

A contrast collar always adds what we in the business call some “visual interest” up top, but this classic denim bad boy hardly needs it. 

Raglan Topcoat

Gap gap.com

$228.00 $122.97

Gap once again demonstrating exactly how you should rock its expertly styled products this season and, really, any season after it. 

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Avidan Grossman is the Style eCommerce Editor at Esquire, covering men’s fashion, shoes, grooming, and accessories.

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Source : Esquire