48 Best Prime Day Clothing Deals 2023: Killer Menswear From Calvin Klein and Levi's

For every other worthwhile deal we’ve found, head over to our massive list of the best early Prime Day Deals 2023 has to offer. And check out the rest of our pre-Prime Day coverage, broken out by category, below.

The Best Prime Day Menswear Deals | The Best Prime Day Tech Deals | The Best Prime Day Luggage Deals | The Best Non-Amazon Menswear Deals | The Best Prime Day Shoe Deals | The Best Prime Day Furniture Deals | The Best Prime Day Fitness Deals | The Best Prime Day Vacuum Deals | The Best Prime Day Deals Under $25 | The Best Prime Day Grooming Deals | The Best Prime Day Watch Deals

Prime Day Favorites

From fall-ready flannels to evergreen blue jeans to extra cozy hoodies, the prime day menswear deals leave no fashion category untouched.

Portuguese Flannel

Flannel shirts don’t have to come in plaid, ya know.


Nobody has to know these didn’t really come from the ’90s.


Classic Fit Signature Lux Cotton Stretch Pants

Them fancy schmancy wide-leg pants don’t have to come from a capital-F Fashion store.

Lands’ End

Your front row ticket to the prep revival.

Brooks Brothers

Non-Iron Stretch Oxford Sport Shirt

A blue Oxford cloth button down shirt is like required reading, but for your closet.


501 Original Shrink-to-Fit jeans

We present to you your new raw denim fade project.


Say “howdy” to your new honkey tonk jeans.


Reverse Weave Fleece Hoodie

They don’t call it Champion for nothin’!

Prime Day Outerwear Deals

The beautiful autumn leaves aren’t the only things we’re excited about this season—it’s finally cool enough to layer up and these Prime Day jacket deals make sure your style stays lit without burning through your bank account.

Carhartt WIP

Cropped work jackets like this will never not be popular—but they don’t always go on sale.


It’s jackets like this that made guys like Steve McQueen menswear legends.


Faux Leather Trucker Jacket

Probably the coolest jacket you’ll come across on Amazon.

Mountain Hardwear

Channel your inner Michelin man.


Essentials Warm-Up 3-Stripes track jacket

Blast some Oasis and let the blokecore wash over you.

The North Face

Insulate yourself from chilly weather and bad fits.


Ascender Softshell Front-zip Jacket

A windy day makes any weather worse—this jacket makes up for it.


Tomato season was great, but now is it’s all about hoodie season.

Prime Day Shoe Deals

It’s really a shame that we only have two feet because there just too many great shoes to enjoy and the Prime Day shoe deals are just the tip of the iceberg. Whether you’re in need of a new pair of gym shoes, looking to dress up your outfits with a pair of loafers, or preparing to trek through some tough trails, these shoe deals will put your best foot forward.


Good for piling on the miles; great for anchoring a fit.

Cole Haan

Polishing up your fits doesn’t have to break the bank. Cole Haan’s ever-stylish Pinch loafers will add a dash of old man steez (by way of Tyler, the Creator) for just about a hundred bucks.


If these were good enough for hip-hop royalty, they’ll be good enough for you.

R.M. Williams

Classic RM Leather Chelsea Boots

The prefect boot to stride into your sexiest era.


Bet you didn’t know Oakley also made sick kicks, huh?


The Samba train still has plenty of steam as far as we’re concerned.


Moab 3 Mid Waterproof Hiking Boot

The difference between the good outdoors and the great outdoors is a really solid pair of boots.

Muck Boot

Muck Wetland Rubber Field Boots

Prime Day Watch Deals

There’s never a bad time for a good watch deal. That said, there are better times. With watches as popular as ever, Prime Day watch deals couldn’t have come at a better time.


96D138 Chronograph Quartz Watch

This watch probably belongs on the wrist of an international super spy with a palate for shaken martinis.


Promaster Dive Automatic 3 Watch


5 Automatic SRPE61K1 100m Watch

An every-day watch with a not-so-every-day gray sunburst dial that catches the light nicely.


SWR049 Essentials Collection Watch

Good enough to make you forget that Tank you’d been ogling.


Siri, where’s the best place to flex my new watch?


Sutton Automatic Alligator-Grain Leather Strap Watch

And the award for prettiest watch on Prime Day goes to…


Essential Stainless Steel Green Dial Watch

The perfect mix of rugged and elegant, wound into one gorgeous ticker.


G-Shock GMB2100D-1A Watch

Just when you thought the viral CasiOak watch couldn’t hit any harder, the all-metal version proves how wrong you are.

Prime Day Basics Deals

Every menswear god has the basics down pat. And now that the Prime Day basics deals are out, there’s no excuse for a sorry closet full of bad tees and busted underwear.


Don’t overcomplicate your sock situation: just get plain white socks.

Calvin Klein

Cotton Stretch Boxer Brief (5-Pack)

Be real with yourself: you need new undies.


EcoSmart Fleece Sweatshirt

Use those brain smarts and rake in the savings on this toasty sweater while you can.

Polo Ralph Lauren

Classic Fit Woven Cotton Boxers

The only thing that could make our favorite boxer shorts better is a deal.

Calvin Klein

Cotton Classics 5-Pack Undershirts

Keep your nice button-up shirts fresh and clean—wear an undershirt.

Polo Ralph Lauren

Classic Fit Cotton Tanks 3-Pack

Just because we’re in fall doesn’t mean tank season is over!


Midweight Long Sleeve Thermal Shirt

Tossing on this merino wool base layer is about as coz as fresh apple pie.


Essentials Single Jersey 3-Stripes T-Shirt

Who said your basic tees have to be, well, basic?

Prime Day Accessories Deals

Leaving out the accessories from your outfit is kind of like forgetting the candles on a birthday cake. These Prime Day Accessories deals will get you sorted, from sunglasses to jewelry to bags and more.


PO0649 Aviator Sunglasses

If it’s good enough for F1 drivers, these sunnies can handle your above-average walking pace.


Tennis deluxe collection tennis bracelet

You watch tennis because you like the sport. Surrrrreeeee.


RB2140 Original Wayfarers

Homme Plissé Issey Miyake

L’eau D’issey Eau de toilette

Like seasonal vegetables, fragrances are more enjoyable when they come around once a season.


Herschel Novel Duffel Bag

Consider this your dream weekend getaway in the bag.


Styling is a cinch when you’ve got the right belt.

The North Face

At last, beanie season is here.

Ralph Lauren

Polo Black Eau de Toilette

Looks like they’ve managed to bottle ‘sexy’ and ‘mysterious’ into a fragrance.

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