The 50 Best Prime Day Menswear Deals Under $50

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I know you're probably busy with a dozen other Amazon tabs open this Prime Day (sorry, this time around it's called Prime Big Deal Days). But, let me keep this short and sweet. While you're scoring new tech, home, and kitchen items from Prime, don't forget to get secure some seriously good fashion pieces at a discount, too!

For today only, Amazon Prime's Big Deal Days deals (mouthful, wow) are off the charts. Seriously—when else could you get all this menswear for $50 or less? This is a great time to refresh your wardrobe with staple pieces, from basics as simple as underwear to performance clothes for your next workout to a fresh button-down for that big meeting you have coming up. These are 50 of the very best Prime Day fashion deals, and they cost less than your next meal will.

Essentials 3-Pack 100% Cotton T-Shirts

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

Venice Burnout Notch Neck Tee

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

Stretch Chinos

Chino season is here, after all.

501 Original Fit Jeans

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

Dress Shirt

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

Tiro 21 Track Pants

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

Long-Sleeve Soft Touch Quarter-Zip Sweater

For all those cozy fall days where you can't be bothered to put more effort into layering.

Full-Zip Hooded Fleece Sweatshirt

Everyone needs a zip hoodie—especially at this price.

Ace Cargo Pant

Today's your last chance to snatch these chic, durable Levi's cargos for just around 40 bucks.

Pallas Short Sleeve Polo Shirt

At nearly half off, this polo is a definitive "add to cart" piece in my books.

Pashmina Scarf

If you're going to wear a winter scarf, it might as well be Calvin Klein, right?

Short Sleeve Polo Shirt

An everyday, versatile polo so good, you should probably stock up on a few different colors.

Long Sleeve Solid Oxford Button Down Shirt

And if you're feeling especially chic, throw in the OCBD, too.

Extreme Motion Flat Front Relaxed Taper Pant

Whether you're traveling or heading into the office, these relaxed-fit, stretchy pants are more than ideal.

Impact Run 5 Inch Short

Buy yourself a coffee with the money you saved on these shorts after your next run.

Rival Fleece 1/2 Zip Hoodie

Warm, roomy, and soft, this hoodie truly has it all.

Entrada 18 Jersey

At only 15 bucks, this is sure to be the most affordable part of your workout look.

Zip-Up Hoodie

You can never have too many WFH hoodies. I speak from experience.

Classic Asterisk T-Shirt

Whereas band merch is usually upwards of 50 bucks, you can snag this sick, iconic tee for less than 20.

Golf Standard UPF Quarter Zip Pullover

This looks just as good on the green as it does off of it.

Golf Standard UPF Long Sleeve Polo Shirt

A long sleeve polo keeps the classiness in golf, but takes out the part where you shiver through your game.

Golf Provisional Pant

And, hey—if any golf pants are up for it, it's this Adidas pair.

Long Sleeve Vintage Whale Pocket T-Shirt

A comfortable, casual classic.

Short Sleeve Vintage Whale Pocket T-Shirt

Plus, the iconic t-shirt that'll never be out of style.

Crewneck Sweatshirt

No winter wardrobe is complete without a basic, go-to sweatshirt.

Short Sleeve Linen Johnny Collar Polo

This linen polo is so damn nice, it's going to be the first thing you pull out of your closet come springtime.

Slim-Fit Stretch Jean

A staple pair of jeans that are actually comfortable.

Slim-Fit Long-Sleeve Henley Shirt

Meet the T-shirt's cooler older brother: the henley.

Crew T-Shirts 5-Pack

At just around 15 bucks, these 5 tees come in at roughly $3 apiece. A damn good deal if I've ever heard one.

Stadium Packable Jacket

For long days spent outside, a windbreaker is an absolute must-have.

Fleece Joggers

Lounging around just got a cooler look.

Short Sleeve Metallic Buddha Tee

One of the OG purveyors of the cool graphic tee has a Prime Day option for only $35.

Branded Collar SS Polo

Kinda sporty, kinda chic, this stylish polo is a Prime Day favorite.

Buffalo Plaid Knit Shirt

For all your fall layering needs.

Dress Shirt

Another dress shirt option—but with a pocket!

Solid Crew Neck Short Sleeve

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

Ultra Loft Quilted Puffer Vest

That extra dollar for this $51 vest is so worth it on chilly autumn mornings.

Paul Curved Logo Polo Shirt

You'll look fresh as hell wearing this into the office later this week—and yes, this week, because Prime shipping is that fast.

410 Athletic Fit Jeans

At just about 60% off, these Lucky Brand dark wash jeans are a classy steal.

T-Shirt

Say hello to your new favorite graphic tee.

3-Pack Cotton Stretch Boxer Briefs

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

Fleece Joggers

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

Wade Leather Bifold

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

Sherpa Trucker

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

Easy Reader 35mm

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

Weekender

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

Beefy T, 2-Pack

The best t-shirt of all time.

Boxer Brief 3-Pack

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

Cowboy Cut

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

Wrancher Dress Jeans

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.

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