18 October Prime Day Style Deals Under $50 You Can Only Shop Today

Timex Easy Reader 35mm

Now 30% Off

A simple, good looking watch for $35? It’s an incredible deal.

Timex Weekender

Now 32% Off

You know what, go ahead and buy the Timex field watch too.

Lacoste Essentials 3-Pack 100% Cotton T-Shirts

Now 33% Off

Not one, not two, but three Lacoste tees! Talk about a steal.

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Hanes Beefy T, 2-Pack

Now 69% Off

The best t-shirt of all time.

Calvin Klein Boxer Brief 3-Pack

Now 31% Off

I got #MyCalvins on sale because I’m fiscally responsible and generally worried about the state of the economy.

Levi’s 501 Original Fit Jeans

Now 48% Off

Bet you didn’t see these coming. Get a classic, iconic pair of Levi’s for under 50 bucks.

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Wrangler Cowboy Cut

Now 24% Off

Or pick up some Wranglers with a little flair to go more Western, more 70s with it.

Wrangler Wrancher Dress Jeans

Now 46% Off

Or, go for the cleaner looking version that had TikTok fashion in a chokehold a few years back. Same slight flair, high rise, and flattering look.

Levi’s Sherpa Trucker

Now 46% Off

Ok sorry, it’s $8 over, but it’s a great deal and every guy needs one of these.

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Champion Fleece Joggers

Now 58% Off

It’s not everyday you get this amount of comfort and coziness for under 20 bucks.

Fossil Wade Leather Bifold

It’s not everyday you can get a brand new leather wallet for a price like this.

Lucky Brand Venice Burnout Notch Neck Tee

Now 30% Off

This tee feels pre-worn in, so you’re guaranteed all-day comfort.

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Adidas Tiro 21 Track Pants

Now 11% Off

Adidas track pants for less than $30? Prime Day should be a national holiday.

Calvin Klein Dress Shirt

Now 46% Off

This designer dress shirt will only set you back, like, two Starbucks orders.

Nautica Solid Crew Neck Short Sleeve

Now 36% Off

This casual pocket tee is perfect for lazing about in summer and layering up in fall.

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Lacoste 3-Pack Cotton Stretch Boxer Briefs

Now 47% Off

With Prime Day’s discount, each pair of Lacoste boxer briefs in this 3-pack averages out to less than $10.

Van Heusen Dress Shirt

Now 29% Off

Another dress shirt option—but with a pocket!

Tommy Hilfiger Stretch Chinos

Now 36% Off

Chino season is here, after all.

Trishna Rikhy

Trishna Rikhy is the Associate Style Commerce Editor at Esquire. Previously, her writing has appeared in Vogue Runway, PAPER Magazine, V Magazine, V MAN, and more. She is based in NYC, but can probably be found wherever the strongest cup of coffee is.

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