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    60+ Best Prime Day Clothing Deals in 2025, According to GQ

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    60+ Best Prime Day Clothing Deals in 2025, According to GQ

    Last Updated 7/8/2025 at 3:02 p.m. ET: Prime Day is officially here—and this year, Amazon’s not holding back. For the first time ever, the sale’s running four full days, from July 8 through July 11. The discounts are already flying, and the GQ Recommends crew is combing through the Everything Store to bring you the very best Prime Day clothing deals.

    We’ll be updating this page around the clock as prices drop, so check back often. And if you’re looking for more reasons to open up your wallet, be sure to check out our massive list of the best Prime Day deals worthy of your attention.

    Featured in this article
    The No-Brainer Undies

    Calvin Klein Cotton Stretch Boxer Briefs (3-Pack)

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    Our Favorite Prime Day Clothing Deals

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    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.

    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.

    Levi’s

    Classic Western Shirt

    Almost as classic as their beloved blue jeans, the Levi’s western shirt is an instant way to add a ton of swagger to every outfit.

    Madewell

    Workwear Overshirt

    Thanks to Prime Day, you can now underpay for this overshirt. Pair it with some cutoff shorts and leather sandals and you’ve got the ideal summer fit.

    Umbro

    Checkered Shorts

    Mic check, 1, 2, 3, 4 pairs of shorts at this Prime Day price.

    Beaudrm

    Mesh Football Jersey Shirt

    Have we ever heard of Beaudrm? No. Do we like this mesh football jersey and think it’ll absolutely hit during sweltering summer days? Yes.

    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.

    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.

    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.

    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.

    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.

    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.

    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.

    Prime Day Basics Deals

    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.

    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.

    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

    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.”

    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.

    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.

    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.

    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.

    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.

    Carhartt

    Rain Defender Loose Fit Heavyweight Sweatshirt

    Not only does Carhartt’s triple-beefy hoodie defend from rain, it defends from bad outfits.

    Prime Day Shoe Deals

    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.

    Puma

    Speedcat OG Sneakers

    The Puma Speedcat OG launched in ’99, inspired by classic motorsport gear. With its low profile, suede build, and sleek lines, it’s a throwback that’s a worthy addition to any sneaker rotation.

    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.

    Brooks Brothers

    Campus Loafer

    Of course Brooks Brothers makes a “Campus” loafer—it practically invented the campus uniform. This one’s sleek, sturdy, and classic enough to make you feel like the big man on campus (again).

    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.

    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.

    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.

    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.

    Dr. Martens

    Adrian Loafer

    The Adrian combines all the edge of a combat boot with the polish of a dress loafer. Easy to wear, hard to beat.

    Chaco

    Z/1 Classic Sandal

    The cool crunchy sandals you’ve seen on your avid hiking friends and in extremely stylish Japanese fashion circles.

    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.

    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.

    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.

    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.

    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.

    Persol

    PO3059S Square Sunglasses

    Ditch the usual Aviators and grab these Steve McQueen-approved shades instead.

    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

    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.

    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.

    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

    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.

    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.

    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.

    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.

    Prime Day Clothing Deals FAQ

    What should I expect from Amazon Prime Day 2025?

    For the first time ever, Amazon Prime Day is slated to be four days long. Except steep cuts on basics (white tees, polos, denim), activewear, sneakers, and outerwear. Brands like Levi’s, Calvin Klein, Dickie’s, and Lacoste tend to unload a lot of inventory. Prime Day is also low-key a great opportunity to snag a new watch, as well as a new cologne.

    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 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.

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