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.
Lacoste
Classic Long Sleeve Pique Polo Shirt
Polos don't stop in winter, their sleeves just get longer.
Dickies
Relaxed Straight-fit Cargo Work Pant
Who needs a bag when you've got cargo pants?
Thorogood
American Heritage 6" Steel Toe Work Boot
New Era
MLB Core Classic 9TWENTY Cap
When you're having a bad hair day and you're not a beanie guy.
Lands' End
Classic Fit Fine Gauge Supima Cotton V-Neck Sweater
V-neck T-shirts—still not cool. V-neck sweaters, very much cool.
Polo Ralph Lauren
Signature Italian Virgin Wool Scarf
Mountain Hardwear
Outpost Long Sleeve Line Shirt
We love it when the shirts turn plaid in the fall.
Reigning Champ
Midweight Terry Slim Sweatpants
Reigning Champ's high-level sweats are well worth the price tag (even more so on the rare occasion they go on sale).
Faherty
Unlike those dress shoes with running shoe soles, this hybrid sweater-shirt actually works.
Portuguese Flannel
Flannel shirts don't have to come in plaid, ya know.
Levi's
Nobody has to know these didn't really come from the '90s.
Dockers
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.
Levi's
501 Original Shrink-to-Fit jeans
We present to you your new raw denim fade project.
Wrangler
Say “howdy” to your new honkey tonk jeans.
Champion
Reverse Weave Fleece Hoodie
They don't call it Champion for nothin'!
Gap
Long Sleeve Chambray Woven Button-Down Shirt
Like a pair of blue jeans, a chambray shirt can really go with any aesthetic.
Club Monaco
Long Sleeve Solid Oxford Shirt
Main Street Forge
Made in USA Heavy Duty Work Belt
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.
Oakley
OO4075 Square Wire Rectangular Sunglasses
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.
Arc'teryx
Kyanite Lightweight Hoody
As if the Arc'teryx pedigree wasn't enough to turn heads, the hi-vis orange will snap some necks.
Marmot
Toss on your favorite hoodie underneath and you're officially the coziest dude on the block.
The North Face
Textured Cap Rock ¼ Zip Pullover Sweatshirt
The light layer you were looking for to survive this weird in-between weather.
Alpha Industries
Apollo L-2B Flight Jacket
Carhartt WIP
Cropped work jackets like this will never not be popular—but they don't always go on sale.
Baracuta
It's jackets like this that made guys like Steve McQueen menswear legends.
Levi's
Faux Leather Trucker Jacket
Probably the coolest jacket you'll come across on Amazon.
Mountain Hardwear
Channel your inner Michelin man.
Adidas
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.
Columbia
Ascender Softshell Front-zip Jacket
A windy day makes any weather worse—this jacket makes up for it.
Levi's
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.
Reebok
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).
Blundstone
These sturdy leather boots decked out with a shock-absorbing rubber sole were made for stompin' and that's exactly what you'll do.
Dan Post
Renegade Round Toe Casual Boots
If Amazon had a brick and mortar, you'd be clicking your heels all the way home with these swanky boots.
The North Face
Sleeping bags for your feet it turns out, is a very good idea.
ASICS
Good for piling on the miles; great for anchoring a fit.
Cole Haan
The quickest way to class up every outfit is a solid pair of tassel loafers.
Clarks
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.
Oakley
Bet you didn't know Oakley also made sick kicks, huh?
Adidas
The Samba train still has plenty of steam as far as we're concerned.
Merrell
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.
Bulova
96D138 Chronograph Quartz Watch
This watch probably belongs on the wrist of an international super spy with a palate for shaken martinis.
Citizen
Promaster Dive Automatic 3 Watch
This seamaster ilooks pretty damned good on dry land.
Skagen
SKW6852 Grenen Three-Hand Watch
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.
Casio
Watches really don't get much cleaner than this.
Seiko
5 Automatic SRPE61K1 100m Watch
An every-day watch with a not-so-every-day gray sunburst dial that catches the light nicely.
Seiko
SWR049 Essentials Collection Watch
Good enough to make you forget that Tank you'd been ogling.
Apple
Siri, where's the best place to flex my new watch?
Bulova
Sutton Automatic Alligator-Grain Leather Strap Watch
And the award for prettiest watch on Prime Day goes to…
Seiko
Essential Stainless Steel Green Dial Watch
The perfect mix of rugged and elegant, wound into one gorgeous ticker.
Casio
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.
Tissot
PSA: you can buy a Swiss made watch for way less than you think.
Orient
"Bambino Version 8" Japanese Automatic/Hand Winding Watch
Orient's under-the-radar status means you've found your new come up.
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.
Goldtoe
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.
Hanes
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!
Meriwool
Midweight Long Sleeve Thermal Shirt
Tossing on this merino wool base layer is about as coz as fresh apple pie.
Adidas
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.
Cremo
"Palo Santo" Spray Cologne
Like your AM mindfulness routine, in a bottle.
Bellroy
Chasing paper means your bank account gets bigger, not your wallet.
Persol
PO0649 Aviator Sunglasses
If it's good enough for F1 drivers, these sunnies can handle your above-average walking pace.
Swarovski
Tennis deluxe collection tennis bracelet
You watch tennis because you like the sport. Surrrrreeeee.
Ray-Ban
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
Herschel Novel Duffel Bag
Consider this your dream weekend getaway in the bag.
Arc'teryx
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.