The Best Prime Day Clothing Deals You Can Shop Early

We know what you’re thinking: early Prime Day clothing deals…again? Believe it, buddy—it sure seems like Bezos is just as starved for new IP as the bigwigs in Hollywood. This time around, though, Amazon insists on calling its October 2024 APD redux “Prime Big Deal Days” (Prime Day 2: 2 Prime 2 Days must’ve been taken) but the basic pitch is still the same: a two-day bonanza packed with bargains on everything the, uh, Everything Store has to offer. (You can read up on the specifics here.)

No matter what you call it, though, Prime Big Deal Days officially kicks off the morning of October 8th and will stick around until midnight of October 9th. If you can’t be bothered to wait until then, relax: There are tons of ~~Amazon Prime Day~~ Prime Big Deal Days discounts on wardrobe-boosting menswear right this very second. And because Amazon is a digital jungle that remains reliably impossible to hack through, we enlisted the savviest deal-hunters in the GQ braintrust to scope out the terrain for you. Happy shopping!

The Best Prime Day Clothing Deals Right Now

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Look, if you want the triple-distilled version of all the best early Amazon Prime Day clothing deals, here they are: a short list of our absolute favorite discounted duds you can cop right now—from GOAT-worthy denim to fall-ready zip-ups to pleasantly hefty kicks, and so much more.

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.

Lacoste

Classic Long Sleeve Pique Polo Shirt

Tennis may be hotter than ever, but these iconic polos never went lukewarm.

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.

Russell Athletic

Dri-Power Full Zip Hoodie

A classic is a classic is a classic is a classic.

Early Prime Day Shoe Deals

We know that Amazon ain’t exactly “it” when it comes to the menswear space. There are, however, a couple of select areas that the Everything Store truly excels in. Primary among them? Shoes. You won’t find any sneakers worth lining up for, but you will find a slew of classic kicks that look great in any context.

Sperry

Authentic Originals Boat Shoes

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

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.

Adidas

Samba Classics

You won’t find the Samba OGs on sale during Prime Big Deal Days, but the Classics, with their extended tongue, are the next best thing.

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.

Early Prime Day Watch Deals

Affordable watches are better than they have been in years, but if you don’t want to go down that particular rabbit hole, Amazon boasts a surprisingly killer selection of tickers that tend to get the discount treatment on Prime Day. You can expect to see bargains on approachable bangers from the likes of Timex, sure, but if you’re lucky, you can also snag serious savings on the heirloom-grade Hamilton your grandkids will be stoked to inherit.

Seiko

SRPG35 Watch

Your first step toward horological greatness is none other than the Seiko 5 series, a budget style move that’s served as the gateway for many a serial watch enthusiast.

Timex

Weekender Analog Dial Watch

Rugged nylon strap, handsome French vanilla watch face, and clean lines throughout. Now that’s one hell of a way to spend your time on the weekend.

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.

Casio

MW240-1BV Easy to Read Analog Display Quartz Watch

There’s beauty in simplicity and this no-frills resin watch from Timex is the dictionary definition of simple.

Early Prime Day Basics Deals

When it comes to menswear, Chez Bezos nails the basics. Which means Prime Day—no matter what Amazon is calling it—remains the ideal time to stock up on foundational staples like underwear, T-shirts, and socks from a who’s who of the best brands in each genre.

Calvin Klein

Cotton Classics Boxer Briefs (5-Pack)

We like to think of these Calvin Klein boxer briefs as the Levi’s 501 of underwear. They’re classic, they look great on just about everyone, and they are a menswear necessity.

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.

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.

Fruit of the Loom

Sleeveless Tank (6-Pack)

Mamma mia! The weather is blistering and the only way to deal with it is to fight fire with fire and wear an incredibly hot tank.

Early Prime Day Accessories Deals

Forget that old Coco Chanel chestnut about taking one thing off before you head out the door: No outfit is complete without an accessory or two, the sartorial cherry on top of your already-tasty sundae. Need a gleaming pair of shades to protect your peepers from the waning fall sunlight? Amazon’s got you covered. How about a compact wallet to replace your Costanza-like bifold? Amazon’s got your back—literally—in that department, too.

Calvin Klein

RFID Leather Minimalist Bifold Wallet

Cash ain’t going away, so while your fancy digital wallet and tap-to-pay cards are enjoying their time in the sun, having some IRL money is still worth it. For that, get yourself a wallet that can handle all forms of currency in a handsome form factor.

Oakley

Whisker Oval Sunglasses

Time to tap into your inner Y2K baddie. Now all you need is are some baggy cargo pants, chunky sneakers, and some drum-n-bass.

Early Prime Day Outerwear Deals

Fall isn’t on the horizon, folks: it’s here. Which means it’s high time you start thinking about your outerwear situation (and, y’know, really start dressing). Amazon isn’t the first place we’d direct you towards, but if your cold-weather rotation is in dire need of a refresh, the retailer’s assortment of weatherproof zip-ups will keep the chill at bay until you’re forced to dust off the parka.

Adidas

Essentials Warm-Up 3-Stripes Track Top

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

Outdoor Research

Helium Rain Jacket

Like it or not, rain still happens even in the middle of summer. So stash this in your bag if those clouds you’re seeing look like a gamble.

Arc’teryx

Atom SL Hoodie

The gorp-y gods at Arc’teryx are indeed available at Amazon. So when you step into that subzero theater for some respite from the heat, bring this along.

Oakley

Endurance Packable Jacket

If you only know Oakley for its roster of diesel-fueled sunglasses, you don’t know jack. The iconic eyewear brand also makes incredibly cool clothes.

Amazon Prime Day Clothing Deals FAQ

What were the best deals from the first Prime Day?

We’re pretty good at predicting trends, but even our well-polished crystal ball gets a little hazy. We can’t say with certainly which deals, exactly, will emerge as the standouts on Prime Day proper, but we do have a solid sense of what to expect based on last round’s best-sellers. If prior history is any indication, you’re in for stellar deals on a slew of household-name brands, including Adidas, Levi’s, Ray-Ban, and more.

During 2024’s first Amazon Prime Day, we clocked steep discounts on Russell Athletic’s iconic sweatshirts, a welcome boon for anyone dreading chillier weather right now. (The fortuitous timing of a bargain on Gold Toe’s cozy crew socks isn’t lost on us either.) We’re also pretty confident Levi’s’ 501 jeans will be at their lowest prices of the year—and that the discounts will extend to the rest of the brand’s catalog, too.

What are the best menswear brands on Amazon?

You can rely on Amazon for affordable menswear of every stripe. If you’re looking for basics, the Bezos-backed behemoth stocks no shortage of quality, GQ-approved wares from Gildan, Russell Athletic, Kirkland Signature, and Reigning Champ. Shopping for a new pair of kicks? Keep an eye on offerings from Adidas, Red Wing, Keen, and Allen Edmonds. Amazon also hawks a surprisingly impressive array of watches from the likes of Casio, G-Shock, Seiko, and TAG Heuer. Oh, and don’t sleep on the retailer’s sunglasses department, which routinely includes A-list shades from Ray-Ban, Illesteva, and Oakley at lower prices than almost anywhere else on the web.

When does Prime Big Deal Days end?

Prime Big Deal Days is a two-day event starting Tuesday, October 8th and ending Wednesday, October 9th. The first batch of deals go live on the 8th at 12:00 a.m. PT (3 a.m. ET). In addition to any deals that roll over, expect a new set of bargains to land on the morning of the 9th, too. The event ends at midnight on October 9th.

Do I need a membership to shop Prime Day?

Yes, you need to be an Amazon Prime member in order to shop the treasure trove of deals offered on Prime Day. If you’re not a member yet, you can sign up for a 30-day free trial here.

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