It’d Be a Crying Shame If All This Discounted Menswear Went to Waste
October 9, 2025
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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’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.
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.