25 Menswear Picks Under $250 to Buy Right Now

One of the many perks of this gig is spending a deeply disturbing amount of my day shopping online, scouring the web for the best bargains money can buy. It’s a digital reality, baby, and there’s no going back! Online shopping is a bit like hitting the biggest all-you-can-eat buffet in the world with no idea what type of food you’re in the mood for. The vastness of the internet means a veritable smorgasbord of steals, deals, and discounts is always but a click away, and figuring out what to put on your plate first can be more than a little stress-inducing.

Should you fill up on chunky sweaters now or save a little room for lightweight outerwear down the line? Should you go back for a second helping of sweatpants or finally try a bite of that corduroy all your friends have been raving about? Should you wait in line at the limited-edition sneaker station or skip straight to the general release table and serve yourself? And, most important, are those boots priced by weight?!

But for the discerning bargain-hunter, shopping online is like deciding what to order at a restaurant you’ve already been to, like, every day for the last five years straight. So—if you’ll indulge the analogy a tad longer—allow me to advise you on the house specialties. Trust me. Like I said, I spend a deeply disturbing amount of my day shopping online.

All of which means I’m well prepared to provide you with the insights you need, starting with some of the sweetest deals you can get your thoroughly rinsed hands on right this very moment—and all for below 250 bucks. Get used it. Because I’ll be updating this list with the tastiest bargains I can find throughout the rest of the season and well beyond, too.

Without further ado…gentlemen: let’s eat.

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Watch Hat

Carhartt WIP endclothing.com

$19.00

Because it’s (finally!) beanie season, and there’s only one reasonable way to celebrate. 

Stretch-Cotton Boxer Briefs (2-Pack)

Calvin Klein Underwear mrporter.com

$24.00

I’m going to go out on a limb here and guess it’s probably time you re-upped on undies. 

Multi Logo Sport Sock (3-Pack)

Polo Ralph Lauren endclothing.com

$25.00

Ditto socks. 

Cozy Knit Sweater

Richer Poorer huckberry.com

$46.98

Adidas Originals Edition Graphic T-Shirt

Wales Bonner ssense.com

$62.00

Sportswear you’ll actually want to rock off the field. 

Samba Sneakers

Adidas x Jonah Hill eastdane.com

$77.00

The beloved actor turned serious auteur (and street-style icon) gets his own Samba. 

Seamless Down Parka

Uniqlo uniqlo.com

$79.90

A parka that’ll help you seamlessly (heh) transition to “holy shit it’s cold out” dressing. 

Thermal Sweatpants

Todd Snyder toddsnyder.com

$99.00

Because sometimes you got to throw up your hands and give the people what they want. 

Heavyweight Popover Hoodie

Todd Snyder + Champion toddsnyder.com

$99.00

See above. 

Maritime Sport MS1 Watch

Timex + Todd Snyder toddsnyder.com

$99.00

The best way make good on your new year’s resolution to cut back on screen time? Invest in a watch (like this particularly handsome one of Todd Snyder’s always excellent collaborations with Timex) and glance at your wrist—not your phone—the next time you need to remind yourself if it’s day or night. 

Truckee Jacket

Knickerbocker huckberry.com

$105.98

Coke white corduroy.  

Tipped Turtleneck Sweatshirt

Todd Snyder + Champion toddsnyder.com

$119.00

A cortado-colored riff on the bona fide turtleneck of the year. 

Sylvester Roll Neck Knit

Howlin’ endclothing.com

$125.00

Meticulously handmade in local Scottish mills, like every sweater named “Sylvester” should be. 

Malthe Turtleneck

Nanushka nanushka.com

$130.00

Interested in turtlenecks but camel tones not your thing? Try one in a darker shade of tobacco brown. 

Thin Screw Cuff Bracelet

Miansai eastdane.com

$136.50

Because nothing pops better over video than a subtle hint of gold. 

Watts Organic Cord Jacket

Far Afield huckberry.com

$139.98

A rugged trucker style designed to up your layering game this winter…

LS Utility Shirt

Universal Works huckberry.com

$144.98

…and the heritage flannel to pair it with. 

+J Wool-Blend Tailored Jacket

Uniqlo uniqlo.com

$149.90

Newfangled pinstripes ready to topple patriarchies and tackle society’s ills, banker-bro reputation be damned. 

Black & Red Femi Track Top

Ahluwalia ssense.com

$156.00

I’m warning you folks now: If one of you doesn’t buy this, I will. 

Brady 6417 Wool Blend Sweater

NN07 nordstrom.com

$189.00

Art you can wear. 

Corbino Print Cotton Button-Up Shirt

Dires Van Noten nordstrom.com

$215.00

Dries don’t miss. 

Heritage Motif Shawl Collar Cardigan

Faherty nordstrom.com

$223.50

Veste Andre Button-Up Shirt Jacket

A.P.C. nordstrom.com

$234.00

So quintessentially French I almost coughed up a perfectly braised coq au vin writing this. 

Walden Combat Boots

Camper nordstrom.com

$238.00

These boots are made for stomping. 

Stretch Wool Blend Water Repellent Topcoat

Bonobos nordstrom.com

$249.00

This coat might not kill fascists (alas) but it will repel almost everything the elements throw its way. 

Expert Style Advice, Every Day

esquire.com

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Source : Esquire