Best Amazon Prime Day Men’s Clothing, Accessories, and Shoes Deals 2021

amazon prime day mens clothing deals


*Sounds trumpets and begins waving flag emblazoned with the Amazon logo*

Amazon Prime Day is nearly here, good people! Ready yourselves! The yearly bonanza is back on June 21 and 22, bringing with it a glut of deals. Deals so quick you’ll blink and miss ’em. Deals so good you’ll stare at them in astonishment. Deals so plentiful that you could conceivably scroll at top speed for the entire event and never reach the end. Deals, man. Deals.

The thing about all those deals, as is the thing thing about Amazon in general, is that it’s harder than many of us would like it to be to separate the wheat from the chaff. It’s great if your cousin Lenny who’s never worn a watch before wants to buy a beater from a brand you’ve never heard of. It’s fine if your barber is really into sweatshirts that feel a little flimsier than you believe a sweatshirt should feel. But you’re a savvy, stylish shopper. You’re not in it for cheap junk, you’re in it for cheap gems.

Instead of sorting through hundreds of pages of search results, just start here. Because even though Amazon Prime Day has yet to arrive—seriously, mark your calendar for June 21 and 22 before you forget—there are already early Prime Day deals aplenty to be found if you click on over to the internet’s everything store. You can score discounted watches, marked-down denim trucker jackets, steals on sweats and sunglasses, and so much more. So start shopping before the hordes descend and get while the getting is good. Then check back for the frenzy (June 21 and 22!) and gird your soul. It’s gonna get a little wild. But that’s half the fun.

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7” Run Short

Peak Velocity


Slim-Fit Long-Sleeve Pique Polo

Amazon Essentials

An unsung hero of the shirting world, the long-sleeve polo absolutely deserves a spot in your closet.

Supima Cotton Stretch Crewneck Undershirts (3-Pack)

Porsche Graphic Leadcat FTR Slide Sandals

Slides? For summer? Groundbreaking. 

AN4266 Lizard Oval Sunglasses

Monogram Logo Jogger Sweatpants

Calvin Klein

Because the pair you’ve been wearing constantly over the last year deserves a break.

Expedition Scout Watch

If there’s a more perfect affordable field watch, I’ve yet to find it.

Suruga Sandals

Go ahead and let those toes take a breather.

Club C Sneakers

A damn good sneaker and a damn good price.

Rally Jacket



For chilly summer nights and every fall day. 

Denim Trucker Jacket

Calvin Klein


Or maybe you’re more of a trucker guy. CK nails it with this washed-down version.

TF-01 Cross Trainer

Pair these with the shorts from earlier for a high-performance, high-style run.

Thick Striped Hooded Sweatshirt

Lay it on (sorry) thick. 

GAS-100B-7ACR Watch

Tough as nails and entirely offbeat, G-Shock has become a modern icon for a reason.

Classic Ivy 35th Anniversary Jacket

Tommy Hilfiger


A true classic from the folks at Tommy.

PH2225 Round Frames

Polo Ralph Lauren


$120.12 (41% off)

If you’re an eyeglasses-wearer, these frames are a steal.

Collider Hybrid Smartwatch



$136.50 (30% off)

A smartwatch that looks so much like a regular watch that it won’t offend your delicate horological sensibilities.

RB4312CH Square Sunglasses



$172.00 (23% off)

OO9428 Frogskins Mix Sunglasses



$184.00 (14% off)

One of Oakley’s greatest hits, Frogskins still look fantastic today.

Startimer Stainless Steel Swiss-Quartz Watch



$275.00 (54% off)

Honestly, I’m a little shocked by how good this deal is. Run, don’t walk.

Patton Boots

Allen Edmonds


$311.50 (27% off)

It’s not often you find supremely well-made footwear at a supremely friendly (for the quality) price.

PRX 316L Stainless Steel Dress Watch



When Tissot goes on sale, you pay attention. Especially when the watch in question looks this good.

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Melinda Krah

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