60+ Prime Day Clothing Deals I’d Buy ASAP, According to My Team of Shopping Experts

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.

We love Comfort Colors’ slate of cotton tees, sure enough. But the real hack is the sweatshirts which feel like a cloud and fit like a dream.

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.

A good henley does it all: layers well and looks great solo. This from the basics specialists at Reigning Champ is as good as they come.

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.

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

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.

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).

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

Golf jackets, harrington jackets, ricky jackets—whatever you call them is up to you. What’s not up to you is the fact that a good one (like this classic joint) will make you a much more stylish guy.

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.

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.

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

Lace ain’t just for frilly gowns and lingerie, as Corridor will be so quick to point out with this camp shirt.

Flannel season is upon us and it helps to have a steady rotation of cozy options at your disposal. This one from Obey is thick, supremely soft, and perfectly relaxed for easy layering.

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.

New Standards are the stuff of denim legend—and has long been our pick for the best entry-level selvedge jeans. Crisp raw selvedge that softens, fades, and only gets better with age.

Puffer season is nearly here and you don’t want to be caught in the freezing weather with a terrible jacket on.

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

Reigning Champ does the basics right—always has. Their midweight terry hoodie nails the formula: soft, structured, and built to last longer than whatever trend comes next.

Rugby shirts are having a serious moment—and for good reason. Levi’s take keeps the look timeless with crisp stripes and sturdy cotton.

The G9 is as timeless as it gets. Baracuta’s iconic Harrington jacket has been worn by everyone from McQueen to Beckham, and this version nails the fit and finish.

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.

A rugged layer with a little farmhand swagger, Levi’s barn jacket nails that in-between-seasons sweet spot.

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.

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.

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

All hail the classic CPO shirt, may its simplicity and utility forever keep you swaggy. This updated version builds upon the OG and updates it in a sweater-like material fo rthe utmost coziness.

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 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.

Hunter’s Chelsea boots take the brand’s iconic rain silhouette and streamline it into an everyday staple—sleek, durable, and just ready for downpours.

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.

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.

These western-tinged boots are a slick deal that doesn’t discriminate—city slickers and real-deal cowboy boys are all welcome.

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.

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

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

Tote bags can be a real drag, but this succinct, compact sling is the perfect size for daily wear. It’s enough for a phone, your wallet, even a book, and won’t impede your well-thought outfit.

Aviators were originally built for the military pilots zooming through the skies. Ever since coming down to Earth, though, their flyness has never descended.

Rag & Bone’s rugged leather belt is the kind of everyday essential you don’t think twice about.

This crescent bag might seem like an unexpected pick, but a bag this size is as practical as all get out.

If you’re serious about performance—or just like looking like it—Oakley’s Radar EVs offer top-tier optics and an unmistakable silhouette.

Sandqvist’s rolltop backpack combines clean design with everyday practicality. Made from recycled, water-resistant polyester with leather trims, it’s roomy enough to carry you through the day.

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.

A throwback to the ’90s is always a good idea. Le Spec’s rectangular acetate joints seem perfect with a ratty graphic tee, big baggy jeans and perhaps … some flip flops.

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.

If you don’t already own a G-Shock, there are plenty of good reasons to get one, from iconic looks to apocalypse-proof ruggedness to a mind-bogglingly diverse array of colors and styles. If, however, you need one more reason, check out the price of this Y2K-era DW9052.

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.

Some watches lure you in with the promise of nerdy complications, or, like, a BMI-scanner that also lets you know how subpar your REM is. The Easy Reader takes the opposite track.

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.

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.

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.

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.

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

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

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.

Built for athletes who treat trail maps like suggestions, the Apple Watch Ultra 2 packs 72-hour battery life, enhanced safety features, and pinpoint GPS. Whether you’re deep in the backcountry or just logging miles before sunrise, it’s built to go the distance.