It’d Be a Crying Shame If All This Discounted Menswear Went to Waste

October 9, 2025

All products featured on GQ are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.

Last Updated at 2:45 p.m. ET: Amazon’s Prime Big Deal Days may technically be kaput, but there are enough Prime Day clothing deals still loitering in the digital ether that I’d forgive you for thinking otherwise. Over the last couple of days, I spent approximately half my waking hours doomscrolling Amazon to cherry-pick the very best of ‘em, poring over more product pages than I care to count. If you’re tuning in now, you missed a hell of a lot of discounted menswear. Don’t beat yourself up too badly, though: what’s left over is still more than enough to transform any grody schlub into a genuine style god.

I get it: shopping for clothes on Amazon can seem like a fool’s errand. But dig deep enough and you’ll strike gold—like this week’s haul, which included Baracuta’s McQueen-blessed G9 jacket, Merrell’s comfy-fugly Jungle Mocs, heavy-hitting essentials from Gap and Madewell, and everyday upgrades from the likes of Levi’s, Calvin Klein, Dickies, and good ol’ Russell Athletic.

I can’t say for sure how long the Prime Day clothing deals will keep hanging around before Bezos catches on and flips them back to full price, so make moves quick. See something you like? Grab it, and go with god.

GQ-Approved Prime Day Menswear Deals

EDITOR PICK
The Forever Classic
Lacoste Short Sleeved Ribbed Collar Shirt

See the deal

ABSURD DEAL
The Iconic Skivvies
Calvin Klein Cotton Classics Boxer Briefs (5-Pack)

See the deal

EDITOR PICK
The Retro-Doused Sneaker
Reebok Club C Vintage Sneaker

See the deal

Prime Day Basics Deals

Lands’ End

American-Grown Supima Cotton Mock Turtleneck Shirt

Turtleneck season is nigh and we bet you didn’t think you’d find a top-quality Supima cotton version on for a steal let alone on Amazon.

Joe’s USA

Joe’s USA Ringer T-Shirt

A good, plain old ringer tee done right. Soft cotton, contrast trim, nothing fancy—just a classic worth tossing in your cart (and wearing all year).

Russell Athletic

Dri-Power Fleece Pullover Hoodie

The most low-key hoodie in your closet might also be the hardest-working. This one wicks sweat, holds its shape, and zips up with no drama. Russell’s been in the game for over a century for a reason.

Champion

Crewneck Sweatshirt

A sturdy, no-frills classic from Champion that does exactly what a sweatshirt should. Heavy enough for chilly days, light enough for layering—your year-round go-to.

Calvin Klein

Cotton Classics Boxer Briefs (5-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.

Goldtoe

Crew Socks (6-Pack)

Six pairs of plush, cushy socks with a just-right crew length and classic athletic ribbing. Stock up once and forget about buying socks for, like, the next year.

Calvin Klein

Cotton Classics 3-Pack Undershirts

Is it really a surprise to anyone that the brand that makes one of our all-time favorite pairs of underwear also makes a great undershirt?

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.

Champion Men’s 9″ Lightweight Lounge Shorts

These are the kind of shorts you wear when you’re taking a mental health day to recharge.

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.”

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.

Comfort Colors

Short Sleeve Tee

Comfort Colors tees are as close to vintage as it gets, minus hunt. Thick cotton, rich colors, and a broken-in feel.


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.

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.

Brooks Brothers

Friday Sport Shirt

A little less buttoned up, a little more rough around the edges, this tartan shirt from Brooks Brothers is dressed down and ready for a pair of blue jeans and beat-up sneakers.

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.

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.

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.

Levi’s

Western Bomber Jacket

Combining elements of vintage flight jackets and retro workwear coats, this western take on outerwear is tough as nails and easy on the eyes.

Dickies

874 Work Pant

The 874s have been holding it down for decades—tough as nails, crisp as ever, and still the cheapest way to look like you know what you’re doing.

Mountain Hardwear

Plusher Long Sleeve Shirt

Who knew that one of the best plaids would come out of Mountain Hardware?

Lands’ End

Fine Gauge Cotton Cardigan

It’s cardigan season again, and this one from Land’s End is as timeless as they come. Soft, sturdy, and built for layering.

Wrangler

Western Work Shirt

The denim snap shirt that built the West—and half our favorite outfits this year. Wrangler’s Western classic still fits like a dream and ages like good whiskey. Yeehaw optional.

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.

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.

Wolverine

Men’s Work Shirt

We can’t decide if we love it or hate it—but either way, it’s crazy discounted. Sometimes a deal’s just too good to overthink.


Prime Day Shoe Deals

Vans

Fillmore Sneakers

Whether you can kickflip or not is irrelevant. SoCal’s sneaker brand of choice will make sure you can look the part and that no real-deal skater will question your skills.

Converse

Chuck Taylor All Star High Top Sneakers

Peep any old-school lifting video from the 90s and you’ll see both powerlifters and bodybuilders rocking Chucks. That’s because their flat, stable base is great for lifting.

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 70 Low Sneakers

The Chuck 70 is an all-timer—undefeated, unbothered, and as versatile as ever. Born on the basketball court and adopted by every cool subculture since, it still goes with everything you own.

Wolverine

I-90 Boots

Wolverine’s burly Chelsea boots are built like a tank and look like a dream.

Merrell

Jungle Leather Slip-Ons

The Jungle Mocs are one of our favorite fugly sneakers in that they are practical and weirdly, well, ugly. They slip on easy, feel incredible underfoot, and go with just about everything.

New Balance

997 Sneakers

Every generation has its New Balance and for the hip Millennial crowd, it’s the 997.

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.

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.

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.

Sperry

Authentic Originals Boat Shoes

Boat shoes are undeniably one of the most controversial trends of the summer. Why not spark some conversation?

Eastland

Falmouth Four Eye Camp Moc Oxford

If the boat shoe craze has you intrigued but you can’t fully dive in, try out these moccasin lace-ups instead.


Prime Day Accessory Deals

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.

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.

Perry Ellis Portfolio

Braided Leather Belt

Behold, a belt that has it all: woven leather, silver-toned hardware, a western flair, and a damned good price tag to boot.

Ray Ban

Wayfarer

It doesn’t get any better than the OG Wayfarer from Ray Ban. These iconic shades come in a wide range of colors and pair well with everything from your summer grubbies to dressed-up date nights.


Prime Day Watch Deals

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.

Timex

Marlin Chronograph Watch

Alongside trucker jackets, tie-dye tees, and huaraches, motorsports watches were among the greatest style hits of the late 1960s. This one captures all of the essential features of the genre, from the racing green dial and rally strap to the stopwatch function and tachymeter bezel.

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.

Citizen

Garrison Super Titanium Watch

By our calculations, if a titanium watch is good, then a Super Titanium watch ought to be several orders of magnitude better. However the math works out, it’s hard to argue with the no-nonsense looks and ethereal lightness of this one, to say nothing of the deeply discounted price.

Timex

Expedition Scout 40mm Watch

There’s beauty in simplicity after all, and Timex’s small-but-mighty resin watch is the dictionary definition of simple.

Seiko 5

Automatic Sports Watch

We’ve yet to encounter an entry-level ticker with more pedigree than Seiko’s legendary sports watch.

Invicta

Pro Diver Collection

Once you finally get around to that snorkeling trip in the Caribbean, you’re going to need a watch as breathtaking as the crystal-blue waters.

Seiko

Presage Watch

With a dial that mimics Japanese garden stones, this Seiko delivers Grand Seiko-level texture and elegance—without the five-figure price tag.

Timex

Q 38mm Watch

Timex’s Q line offers watch geeks direct access to the brand’s archive of retro hits, including this dual-tone quartz beauty, a slightly less buzzy, significantly less pricy alternative to the ‘Pepsi’ Rolex GMT.

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.


Prime Day Clothing Deals FAQ

What is Prime Big Deal Days 2025?

Every year, Prime Day lands in July. This year it stretched across a full four days, from Tuesday, July 8 through Friday, July 11. But starting in 2022, Amazon introduced a sequel event in the fall: Prime Big Deal Days. It’s been back every October since, and in 2025 it returns on October 7 and 8.

Expect steep cuts on basics (white tees, polos, denim), activewear, sneakers, and outerwear. Brands like Levi’s, Calvin Klein, Dickies, and Lacoste tend to unload a lot of inventory, while big-ticket electronics from Samsung, LG, and Sonos headline the markdowns. It’s also a sneaky-good time to start on your gift list—the Everything Store even has a dedicated Holiday Gift Shop, perfect if your holiday gifting strategy is typically panic and prayers.

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.

How long do the deals last?

Prime Big Deal Days 2025 officially kicks off on Tuesday, October 7 at 12:01 a.m. PDT and runs straight through the strike of midnight on Wednesday, October 8. So you’ve got two full days to scoop up as many markdowns as your cart can handle.

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 I need to be a Prime member to shop Amazon Prime Day?

Yes, you must be an Amazon Prime member to access Prime Big Deal Day’s exclusive deals. If you’re not yet a member, you can sign up for a 30-day trial.

Do other retailers participate in Prime Day?

Prime Big Deal Days is an Amazon-exclusive affair. But plenty of other retailers like to ride the coattails with their own competing sales. We’ll keep you posted on the best ones happening at the same time.