78 Best Prime Day Clothing Deals 2023: Menswear for Less

Polos don't stop in winter, their sleeves just get longer.

Who needs a bag when you've got cargo pants?

When you're having a bad hair day and you're not a beanie guy.

V-neck T-shirts—still not cool. V-neck sweaters, very much cool.

Protect ya neck.

We love it when the shirts turn plaid in the fall.

Your Halloween costume is nearly complete…

Reigning Champ's high-level sweats are well worth the price tag (even more so on the rare occasion they go on sale).

Unlike those dress shoes with running shoe soles, this hybrid sweater-shirt actually works.

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

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

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

Your front row ticket to the prep revival.

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

We present to you your new raw denim fade project.

Say “howdy” to your new honkey tonk jeans.

They don't call it Champion for nothin'!

Like a pair of blue jeans, a chambray shirt can really go with any aesthetic.

Black belts with simple silver buckles like this one are the most versatile kind of belt without having to resort to those awful reversible belts you had in high school.

Matrix-level drip.

As if the Arc'teryx pedigree wasn't enough to turn heads, the hi-vis orange will snap some necks.

Toss on your favorite hoodie underneath and you're officially the coziest dude on the block.

The light layer you were looking for to survive this weird in-between weather.

Houston, we have a fit.

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.

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

Channel your inner Michelin man.

Blast some Oasis and let the blokecore wash over you.

Insulate yourself from chilly weather and bad fits.

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.

No, your eyes doth not deceive you. Fall's hottest sneaker is on sale right now, so go ahead and score yourself a pair (or two) or spend the next few months wallowing in regret (just kidding…sorta).

These sturdy leather boots decked out with a shock-absorbing rubber sole were made for stompin' and that's exactly what you'll do.

If Amazon had a brick and mortar, you'd be clicking your heels all the way home with these swanky boots.

Sleeping bags for your feet it turns out, is a very good idea.

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

The quickest way to class up every outfit is a solid pair of tassel loafers.

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

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.

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

Rain, rain, bring it on.

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

This seamaster ilooks pretty damned good on dry land.

That pretty dial is like looking at the vast blue ocean, but don't stare too long—a watch is supposed to keep you punctual.

Watches really don't get much cleaner than this.

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

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

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

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

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

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

PSA: you can buy a Swiss made watch for way less than you think.

Orient's under-the-radar status means you've found your new come up.

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

Be real with yourself: you need new undies.

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

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

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

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

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

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

Like your AM mindfulness routine, in a bottle.

Chasing paper means your bank account gets bigger, not your wallet.

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

You watch tennis because you like the sport. Surrrrreeeee.

Certified classic.

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

Consider this your dream weekend getaway in the bag.

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

At last, beanie season is here.

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