Last Updated 7/10/2025 at 1:30 p.m. ET: Day three of Prime Day is in fully swing, and the deals are looking pretty, pretty … pretty good. ICYMI, Amazon’s stretching the savings across four full days, from July 8 through July 11, which means more chances to score big on closet staples, everyday basics, and a few timely splurges.
But Amazon isn’t the only game in town this week. In between panic-buying garbage bags and comparing undershirt multipacks with the intensity of a sommelier, we’ve been clocking equally impressive menswear discounts across the internet—we’ve included the best of them at the bottom of the page.
Otherwise, the GQ Recommends crew is combing through the Everything Store in real time to surface the best Prime Day clothing deals, and we’ll be updating this page nonstop as new markdowns roll in. If you’re looking to pad your cart even further, don’t miss our giant list of the best Prime Day deals across every category.
Featured in this article
The Jaw-Dropping Undies Deal
Calvin Klein Cotton Stretch Boxer Briefs (3-Pack)
See the deal
The Forever Classic
Lacoste Short Sleeved Ribbed Collar Shirt
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Our Favorite Prime Day Clothing Deals
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Editor Favorite Deals
Russell Athletic
Dri-Power Full Zip Hoodie
A classic is a classic is a classic. The Russell Athletic Dri-Power Full Zip Hoodie nails the basics with soft fleece, moisture-wicking fabric, and an easy fit that goes with everything.
Gap
3-Pack Tank Top
The hottest thing you could wear during summer is also the thing that’ll keep you the coolest. This triple-pack of ribbed tanks is simple, classic, and will turn up the heat on every outfit
Calvin Klein
Cotton Stretch Boxer Briefs (3-Pack)
Our pick for the best underwear to buy in the bulk, Calvin Klein’s stretch briefs are as classic as they get. And there is literally no better time to stock up on them than Prime Day.
Merrell
Moab 3 Mid Waterproof Hiking Boot
A Prime Day MVP, the Moab 3 boot is an all-terrain beast with a reputation for comfort and grip. Lace up and go.
Persol
PO3059S Square Sunglasses
Ditch the usual Aviators and grab these Steve McQueen-approved shades instead.
Seiko
Essentials Watch
The Seiko Tank-style watch toes the line between homage and dupe—but this one lands firmly in the former camp. It’s sharp, affordable, and even better if you catch it on sale.
Dockers
Relaxed Fit Pleated Comfort Khaki Pants
Dockers’ relaxed fit khakis are soft, roomy, and built with stretch—like your dad’s, but in a good way. The pleated front and British khaki tone keep them easy and classic.
Havaianas
Flip Flops
Buying into fashion’s flip-flop propaganda? There’s a pair for every persuasion—including these classic rubber Havaianas. Lightweight, durable, and priced to sell, they’re an option that always makes sense.
New Balance
997 Sneakers
Every generation has its New Balance and for the hip Millennial crowd, it’s the 997.
Levi’s
Harrington Jacket
The Harrington Jacket from Levi’s is about as classic as it gets—short, sharp, and built to layer. Toss it over a tee or oxford and you’ve got a fit that never misses.
Timex
Expedition Scout 40mm Watch
Inspired by vintage army watches, this rugged ticker features a lightweight yet durable webbed strap, vintage white dial, 24-hour display, and subtle glow-in-the-dark hands. It ain’t the steepest discount, but a great buy nonetheless.
Lands’ End
Open Top Canvas Tote Bag
The Lands’ End Open Canvas Tote looks a lot like a certain iconic bag (coughs L.L. Bean) and honestly, it does the trick. Sturdy, roomy, and ready for beach days, errands, or laundry hauls.
Prime Day Basics Deals
Hanes
BeefyT T-shirt (2-Pack)
Undoubtedly one of the best value tees for your money, Hanes’ BeefyT has been going strong for decades thanks to its substantial weight, seamless construction, and great fit.
Polo Ralph Lauren
Classic Fit Woven Cotton Boxers (3-Pack)
For guys who prefer boxers over briefs, Polo Ralph Lauren’s woven boxers are still the gold standard when it comes to price, comfort, and breathability.
Hanes
Cotton Tank Undershirts (6-Pack)
These Hanes ribbed cotton tanks are lightweight, moisture-wicking, and come in a budget-friendly multi-pack. Great as undershirts—or solo when the heat makes anything more feel downright unreasonable.
Tommy John
4″ Second Skin Boxers (3-Pack)
We’ve tested a lot of boxer briefs, and Tommy John’s Second Skin consistently ranks among our favorites. They’re silky-smooth, breathable, and stay put without riding up—a rare trifecta. Multiple testers called them the most comfortable pair they’ve ever worn. If you’re due for a top-drawer refresh, start here.
Champion
Reverse Weave Hoodie
From streetwear obsessives to schlubby-stylish celebs to everyday dudes, the iconic Reverse Weave hoodie will forever be a top tier sweatshirt. The hearty cotton-blend fabric and classic cut come together in a way that countless brands are still trying beat.
Champion
Powerblend Open-Bottom Sweatpants
Among our favorite sweatpants ever, GQ senior commerce editor Avidan Grossman notes: “Champion is the first name in high-quality, low-cost sweats.”
Comfort Colors
1717 Heavyweight Tee
The Comfort Colors tee is a heavyweight champ—thick, soft, and garment-dyed for that perfectly faded look. It’s the kind of shirt that gets better with every wash and feels like an ol’ favorite out the gate.
Carhartt
Rain Defender Loose Fit Heavyweight Sweatshirt
Not only does Carhartt’s triple-beefy hoodie defend from rain, it defends from bad outfits.
Russell Athletic
Relaxed Fit 9″ Shorts
Roomy, breathable, and built to move—these relaxed-fit shorts from Russell are perfect for workouts, grocery runs, or just kicking it around the house.
Goldtoe
Crew Socks (6-Pack)
Caught up in the crew vs. ankle socks debate? Don’t be. The answer will forever and always be crew socks.
Prime Day Fashion Deals
Lacoste
Short Sleeved Ribbed Collar Shirt
If there’s one shirt worth picking up on Prime Day, it’s Lacoste’s signature polo, done up in a now-legendary cotton pique fabric that has endeared it to prepsters and punks in equal measure.
Lacoste
Core Collection Regular Fit Short Sleeve Solid Shirt
PSA: If you didn’t know, camp collar shirts aren’t the only summer shirt.
Portuguese Flannel
Camp Collar Shirt
Why pack this into your suitcase for your summer vacation? Instead, wear it on the plane so you can land at your destination ready to vibe.
Lands’ End
Comfort Waist Pleated 9″ No Iron Chino Shorts
These chino shorts bring serious dad energy in the best way. Built-in stretch, no-iron fabric, and classic pleats make them as easy to wear.
Gap
Denim Utility Shacket
This Gap shacket (their words, not ours) is the ultimate in-between layer—heavier than a shirt, lighter than a jacket, and easy to throw on over anything.
Levi’s
501 Original Fit Jeans
You only need three things to be stylish: a good white T-shirt, a nice pair of shoes, and the one and only original blue jean. We’ve seen the 501s go as low as $30, but that’s quite rare. This is still a great deal if you’re looking to reup on a new pair.
Baracuta
G9 Modern Classic Jacket
If you think we’re gonna stop writing about this jacket, you’ve got another thing coming. Hopefully, it’s this jacket.
Norse Projects
Ezra Relaxed Stretch Twill Shorts 8″
Known for its clean aesthetic with hints of gorpcore and Helmut Lang, Norse Project’s designs are fodder for any moodboard, as you can tell by these streamlined shorts.
Umbro
Checkered Shorts
Mic check, 1, 2, 3, 4 pairs of shorts at this Prime Day price.
Madewell
Waffle Slub Johnny Collar Polo
Waffles, as it turns out, are also delicious as a knit polo. Madewell’s scrumptious and slubby Johnny collar polo is a slick date night move when paired with some tailored trousers and loafers.
Eddie Bauer
Ripstop Shorts
The Eddie Bauer Ripstop Shorts are built for whatever summer throws at you—lightweight, tough, and quick-drying. Great for hikes, travel days, or just showing off some thigh.
Columbia
Brewha II Short
The Brewha II Short nails the vintage vibe with a relaxed fit, washed cotton fabric, and old-school cargo pockets. It’s like your favorite ’90s pair, but built better.
Red Kap
Industrial Stripe Work Shirt
Union or not, this striped shirt is the right tool for the job, even if that job is just heading to the cafe to be perceived by the local baddies.
Colortone
Spider Tie Dye T-Shirt
Add some zest to your everyday basics with this hand-dyed tie-dye T-shirt. At nearly 40% off, we recommend stocking up on your favorite colors.
Adidas
Essentials Warm-Up 3-Stripes Track Top
Ted Lasso will never return (or will it?), but you can bask in this football-approved kit and keep the ball moving.
Adidas
3-Stripes Tricot Opem Hem Track Pants
Fulfill your lifelong dream of becoming the swaggy track coach, all from the comfort of your couch.
Gap
Everyday Soft Stripe Crewneck T-Shirt Tee
Did you know that Gap is on Amazon? Did you know that its ultra plush striped tees are on sale? You’re welcome.
Wrangler
13MWZ Cowboy Cut Original Fit Jeans
The Wrangler 13MWZ is the real-deal cowboy jean, cut straight from the rodeo circuit and tough enough to ride fence all day. High rise, zero stretch, full yee-haw energy.
Corridor
Floral Lace Camp Shirt
Lace ain’t just for frilly gowns and lingerie, as Corridor will be so quick to point out with this camp shirt.
Rhythm
Corduroy Jam Shorts 7.75′
There isn’t really a rule that says you can’t wear corduroy in the summer. The key is to use it well.
Madewell
1991 Loose Straight Jeans
White jeans in the summer is a staple and these cream-colored five-pockets have a loose fit to let the air circulate to keep you cool.
Levi’s
569 Loose Straight Denim Shorts
Tis the summer of baggy denim shorts and there are few out there offering as much as Levi’s does. This 569 cut is very roomy and comes in a gang of great washes.
Gap
Original Straight Fit Denim Jeans
Gap got its fashion footing with denim and, 60 years later, they still do a damn good job at making a pair of dungarees.
Red Kap
Ripstop Crew Shirt
Hard work is good for you, not only for work ethic but for personal style. Case in point—Red Kap’s very non-fashion (but very fashion) work shirt.
Officine Générale
Luis Striped Chambray Camp Shirt
Don’t skip Amazon’s luxury section where you can find bangers like this striped camp collar shirt from modern French label Officine Générale.
Dickies
Relaxed Fit Multi-Use Pocket Work Shorts
Before big baggy shorts were trending on TikTok, Dickies made them a thing on job sites and in SoCal. Respect your elders and buy the OG.
NN07
Kay Pleated Linen Trousers
The lowkey menswear darlings at NN07 know what makes a fashion guy’s heart sing and it’s well-cut, breezy pleated linen pants.
Oakley
Gravity Range Quarter Zip
Oakley may be top dog when it comes to off-the-rails sunnies, but they’re a seriously underrated gorp-y brand when it comes to clothes. Consider this quarter zip your formal intro.
Prime Day Shoe Deals
Puma
Easy Rider Sneakers
With a seriously cool throwback look and an icy cool colorway, Puma’s Easy Riders are the hidden gem of the sneaker world and you won’t have to worry about other people jacking your style.
Reebok
Club C Vintage Sneaker
The Reebok Club C is one of the most underrated and understated sneakers out there. But it’s that restraint that makes them just plain cool.
Converse
Chuck Taylor All Star High Top Sneakers
The Chuck Taylor All Star High Tops are as classic as classic gets. Canvas uppers, rubber toe caps, and endless outfit potential—they’ve been cool for over a century, and aren’t stopping now.
Reef
Cushion Phantom Flip Flop
It’s flip-flop season whether you like it or not. And you know what they say—if you can’t beat ’em, join ’em.
Sebago
Classic Dan Loafers
Like dessert, there’s always space for a pair of loafers. And whether you’re a style maven or a regular Joe, these simple penny loafers are the ones you should have.
Cole Haan
Pinch Penny Loafer
It’s nigh impossible to flub an outfit with a pair of penny loafers, especially when these Cole Haan joints exist. And for this price on Prime Day? That’s what we call pinching pennies.
Deer Stags
Bamboo2 Sandal
Go ahead and get your grandpa swag on. These huarache-style sandals are best served with billowy pants and a flowy linen shirt.
Nisolo
Huarache Sandals
Our favorite pair of summer-friendly, vacation-prone huaraches are on sale, so you can put those extra bucks toward a couple of tropical cocktails.
Dr. Martens
1461 Soft Toe Oxford Work Shoe
The 1461 Oxford blends the brand’s iconic silhouette with work-ready durability. It’s cushy, slip-resistant, and tough enough for long shifts—but still sharp enough to wear off the clock. A true all-day, everyday shoe.
Chaco
Z/1 Classic Sandal
The cool crunchy sandals you’ve seen on your avid hiking friends and in extremely stylish Japanese fashion circles.
Keen
Uneek II Slide Sandal
Delightfully different and freaky cool, Keen’s hiking-enabled webbed slides offer tons of support, traction, and style on and off the trails.
Merrell
Hydro Moc
Built for the water, surprisingly adept as an approach shoe, perfectly suited for dog walking responsibilities.
Prime Day Accessory Deals
Oakley
Radar EV Path Rectangular Sunglasses
If you’re serious about performance—or just like looking like it—Oakley’s Radar EVs offer top-tier optics and an unmistakable silhouette.
Ray-Ban
Caravan Square Sunglasses
The Ray-Ban Caravan is a slept-on classic—clean, squared-off, and a little more low-key than the Wayfarer or Aviator. If you want timeless frames that not everyone’s already wearing, start here.
The North Face
Borealis Laptop Backpack
The North Face Borealis Backpack is built for daily hauls, with a padded laptop sleeve, tons of compartments, and seriously comfy straps. Great for commuting, class, or weekend hikes.
Juli
Sport Sunglasses
Cheap and cheerful, emphasis on both. These sporty shades are the essence of ’90s cool with a sort of JFK Jr. sharpness about them.
Ray-Ban
RB3016 Clubmaster Square Sunglasses
The Clubmasters are a mid-century modern icon—half-frame, all style. They strike the perfect balance between timeless style and everyday wearability.
Troubadour
Apex Compact Backpack
The Apex Compact Backpack trims the fat without cutting corners. Its slim silhouette keeps a low profile, but still fits your laptop, chargers, and daily carry with ease. Water-resistant, well-padded, and handsome enough to make your other bags jealous.
Carhartt
East West Tote Bag
If you thought Carhartt’s work pants were durable, wait til you see what they can do with a tote bag.
Oakley
M2 Frame Sunglasses
No longer are Oakley’s sports-designed shades just for pro-level athletes. Pop these on your face and you’ll feel fast and fly AF.
Prime Day Watch Deals
Casio
LA20WH Watch
When it comes to delivering the absolute most watch for the very least amount of money, no one can touch Casio, whose long-standing dominance in the budget watch bracket is the stuff of legend.
Apple
Watch Series 10
An affordable Apple Watch, this model comes with GPS for enhanced outdoors and sports tracking. It’s crack-resistant, is IP6X-certified dust resistant, and is water resistant up to 50 meters.
Timex
Waterbury Classic Chrono Watch
The Waterbury nails the dress watch basics: clean dial, leather strap, and just enough vintage flair. At 40mm, it’s an easy fit on most wrists—and a no-brainer if you want sharp looks without the splurge.
Skagen
Melbye Three-Hand Day Date Watch
A mid-century minimalist’s dream, Skagen’s grey’d out timepiece is a blast from the past that’s also the perfect wrist accessory for right now.
Seiko
Presage Watch
A subtle-yet-sumptuous dial texture is the hallmark of many four-and five-figure watches (particularly those made by Seiko’s high-end cousin, Grand Seiko). This ticker, however, offers a similar vibe at a much more accessible price, with a dial that mimics the color and texture of paving stones in a Japanese garden.
Seiko
SRPD51 Automatic Watch
Once you finally get around to going on that snorkeling trip in the Caribbean, make sure your watch is as dazzling as the crystal blue waters.
Bulova
Lunar Pilot Chronograph Watch
The Bulova Lunar Pilot riffs on a chrono worn during the 1971 Apollo 15 moonwalk, giving it serious space-age cred—and a rightful place in any earthbound watch rotation.
Tissot
PRX Digital Watch
As anyone who has spent time on r/watches in the last few years knows, the Tissot PRX is a watch with more than its share of fans. Given the near-universal appeal of the PRX’s peak-1970s style, it’s not much of a surprise that it looks just as sharp with a digital display as it does with an analog dial.
Menswear Deals That Aren’t on Amazon
Alex Mill
Easy Shirt
You might buy this for the office, but don’t be surprised when you’re wearing it open over a T-shirt and jeans—or bare-chested and barely buttoned with some shorts—on the weekends. (Alex Mill has 40-70% off more menswear here.)
Engineered Garments
Fatigue Pant
These have just enough linen in them to wear all summer, but still look hardy enough to keep in your rotation through apple picking season.
Abercrombie
Tipped Zip Sweater Polo
Zippers are starting to show up more and more on polos. We’ve been a bit skeptical—but when it works, it works. (Shop Abercrombie’s entire sale, with up to 50% off.)
Prime Day Clothing Deals FAQ
What are the best menswear brands on Amazon?
For affordable fashion across the board, Amazon’s got the goods. If you’re after basics, look to tried-and-true labels like Gildan, Calvin Klein, Russell Athletic, and Kirkland Signature. On the footwear front, you’ll find everything from Adidas sneakers to Red Wing boots to Allen Edmonds dress shoes. The watch selection is equally stacked, with classics from Casio, G-Shock, Seiko, and even the occasional Tag Heuer. And when it comes to sunglasses on Amazon, don’t sleep on Ray-Ban, Chimi, and Oakley. And with more and more inventory from Shopbop (Amazon’s fashion-focused subsidiary) making its way onto the platform, Amazon’s menswear lineup is deeper than you’d expect.
Do I need to be a Prime member to shop Amazon Prime Day?
Yes, you must be an Amazon Prime member to access Prime Day’s exclusive deals. If you’re not yet a member, you can sign up for a 30-day trial.
How long do the deals last?
For as long as we can remember, Prime Day has been a two-day event. Not this year. In 2025, you’ll have four full days to shop for deals. The deals will begin on July 8 and be live through July 11.
Do Prime Day deals change each day?
Yep, Prime Day deals definitely change each day, and sometimes even by the hour. Amazon rotates in new discounts each day across all categories (tech, clothing, home, you name it), so what’s here today might be gone tomorrow. Some deals only last 24 hours, and others sell out with a quickness. If you see something you like, it’s probably smart to grab it before it’s gone.
Do other retailers participate in Prime Day?
While there is only one store participating in Amazon Prime Day (uh, Amazon), there are plenty of other retailers that ride off Prime Day’s coattails. There will be plenty of competitive sales worth perusing, and we’ll make sure we surface those deals up for you. For example, Nordstrom’s Anniversary Sale begins on July 12.
