50 Best Prime Day Clothing Deals 2025 to Upgrade Your Fall Wardrobe

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.

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.

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?

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.

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.

Among our favorite sweatpants ever, GQ senior commerce editor Avidan Grossman notes: “Champion is the first name in high-quality, low-cost sweats.”

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

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.

Polo boxers might not have the cache of Calvin Kleins, but they aren’t far behind. This pack includes 3 pairs of Ralph’s iconic undies for only $40. Good luck finding that price anywhere else.

Dress socks are one of the easiest wardrobe upgrades—and these Polo Ralph Lauren crews are cushy, classic, and primed for all the holiday shindigs filling up your calendar.

An all-around great sock that actually pulls its weight—thick, cushy, and built for the long haul. If you’re clocking serious hours in the cold, these Dickies are the move.

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.

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.

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.

Gap’s Cashoft Quarter-Zip blends cotton and nylon for a cashmere-like feel—soft, smooth, and surprisingly luxe for the price. The perfect layer for the fall temps ahead.

The iconic polo gets all the glory, but this Lacoste V-neck deserves equal shine. Classic, refined, and yes, still rocking that little crocodile right where it counts.

Fulfill your lifelong dream of becoming the swaggy track coach, all from the comfort of your couch.

Ted Lasso will never return (or will it?), but you can bask in this football-approved kit and keep the ball moving.

It’s flannel season, boys. Gap’s boxy long-sleeve version—with a spread collar and dropped shoulders—nails that laid-back look.

Gap’s baggy fit proves what we’ve been saying for a while: Gap jeans are surprisingly good. The fit’s relaxed but not sloppy, with sturdy denim that breaks in just right.

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.

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 workhorse dress shirt with pedigree. Brooks Brothers’ non-iron pinpoint stays crisp all day, with just enough stretch to keep you comfortable.

The easiest way to channel heartthrob energy? This Calvin Klein V-neck. Knit from extra-fine merino wool, it’s soft, sleek, and smooth enough to charm anyone in range.

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.

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

Other Wellies could never—at least not while looking this handsome. Wolverine somehow made a barn-ready boot you could wear to brunch and still get compliments.

A true court classic—clean lines, easy comfort, and Puma’s signature formstrip design on the side.

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.

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).

They don’t call ’em classics for nothing. Reebok’s OG leather sneakers still deliver that perfect mix of retro cool, cushy comfort, and everyday wearability.

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

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

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.

If you thought Carhartt’s work pants were durable, wait til you see what they can do with a 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.

A bunch of Oakleys are marked down for Prime Day, but this pair’s our favorite. The Fives Squared nail that low-profile, high-performance look Oakley built its name on.

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.

This Dickies belt will hold up your fits—literally. Made from tough, full-grain leather with a double-prong buckle that means business, it’s built to last a lifetime of wear.

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

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.

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.

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

Timex’s aptly-named Weekender watch is a triumph of rugged minimalism, the type of ticker that looks just as home poking out from beneath a fraying denim jacket as it does accenting a textured linen suit.

The Seiko 5 Sports has long ruled the under-$500 watch game. This version adds a GMT hand for tracking another time zone—making it a first-rate travel companion, too.

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.

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.

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