15 On-Sale Closet Upgrades Worth Spending Your Holiday Cash On

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Dries Van Noten Reversible Bomber Jacket

A statement piece of outerwear (two, actually) from the king of statement outerwear. —Matt Sebra

$637.50 (was $1,275), available at mrporter.com

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Nike x Fragment Original Tennis Sneakers

A take on the classic on-court shoes that have been an off-court staple for generations (and the new favorite footwear of Shia LaBeouf). — Jake Woolf

$95 (was $155), available at endclothing.com

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Thom Browne check button-down oxford shirt

The best-fitting oxford money can buy, at a price that real guys can actually afford. —Matt Sebra

$152 (was $490), available at ssense.com

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Gap ColdControl Puffer Jacket

You’ll never regret buying a black hooded puffer coat for under $100—even if all you do is wear it to and from the gym. —Megan Gustashaw

$138, take 40% off at checkout, available at gap.com

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Armor Lux Long Sleeve Striped Tee

This is a wardrobe essential for 2017, so we'd suggest buying several while they’re this cheap. —Liza Corsillo

$35 (was $59), available at endclothing.com

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Jil Sander Lace-Up Leather Boots

The most gentlemanly pair of combat boots around and they’ll work equally well with a suit as they do with jeans. —Liza Corsillo

$465 (was $665), available at matchesfashion.com

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Bally Puffer Vest

This retro-inspired ski vest is as eye-catching on the slopes as it would be on a grocery run. —Matt Sebra

$367 (was $875), available at saks.com

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Sasquatchfabrix Twill Trousers

Dickie’s and their designer counterparts were the cool guy pants of 2016, and we can’t see the trend going anywhere quite yet. Plus, that’s the benefit of scooping up items on sale. Should they become lame by summer, you won’t have as much buyer’s remorse knowing you copped them on the low.— Jake Woolf

$158 (was $315), available at Mr Porter.com

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Armando Cabral ‘Sullivan’ Zip Boots

If you still don’t have a pair of tan suede chelsea boots, now’s the time to get yours (there’s really no excuse). —Matt Sebra

$417.00 (was $695.00) + an extra 25% off with code TREATYOURSELF at eastdane.com

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Gant Shadow Check Blazer

When Gant goes on sale pay attention. This very discounted checked blazer will win you compliments for years. —Liza Corsillo

$313 (was $625), available at gant.com

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Orley Floral Polo Shirt

Pick up this knit polo now so you can hit the ground running when the snow finally melts. —Megan Gustashaw

$239 (Was $595), plus take an extra 10% off at checkout, available at barneys.com

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Valentino Side Stripe Pant

You can't do much better than a track stripe pant that wouldn't look out of place at the office, from one of our favorite designer menswear labels. —Matt Sebra

$450 (was $750), available at bergdorfgoodman.com

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Club Monaco Merino Crew Sweater

Now is the perfect time to buy merino and cashmere sweaters in every solid color imaginable. —Megan Gustashaw

$79 (Was $98.50), plus take an extra 40% off at checkout, available at clubmonaco.com

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Maison Margiela Leather Six-Eye Balmorals

Office-appropriate dress shoes that can sit under a suit and jeans—and definitely don’t look like they came from a clearance rack. —Matt Sebra

$289 (was $740), plus an extra 10% off, available at barneys.com

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Needles Velvet Zip Jacket

Velvet, velour, and other uber-cozy fabrics are the statement of the season. And now, it’s easier than ever to embrace your inner Sopranos extra/Paris Hilton from renowned Japanese label Needles. — Jake Woolf

$409 (was $520), available at tres-bien.com

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