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.
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’!
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.
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.
ASICS
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.
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
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.
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.
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.
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