Of all the internet’s many sales frenzies, none go harder—and now longer—than Amazon Prime Day. This year, the mega-retailer is stretching the annual markdown fest to a whopping four days, from July 8 through July 11, the first time it’s ever run that long.
As always, the sheer volume of deals will feel overwhelming—but that’s where your friendly neighborhood shopping experts (that’d be us) come in. We spend all year combing through the Everything Store’s labyrinthine racks, and we’re already on high alert for the best Prime Day clothing deals.
As soon as the prices start to officially drop, we’ll be updating this page with our favorite finds. In the meantime, we’ve pulled together everything you need to know—including a few early gems worth snagging now—so you’re ready when the deals go live.
The Best Early Prime Day Clothing Deals to Shop Now
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Early 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.
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.
Levi’s
Trucker Jacket
Often imitated, never duplicated, the iconic Levi’s trucker jacket is a menswear staple that has the rare ability to look great on just about everyone.
Brooks Brothers
Irish Linen Sport Shirt
A summer staple done right, this Brooks Brothers button-down is cut extra roomy out of Irish linen, so breeziness is guaranteed.
Early Prime Day Basics Deals
Calvin Klein
Cotton Stretch Boxer Briefs (3-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.
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
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.
Polo Ralph Lauren
Classic Fit Woven Cotton Boxers (3-Pack)
For guys who prefer boxers over briefs, Polo Ralph Lauren’s woven boxers are still the gold standard when it comes to price, comfort, and breathability.
Early Prime Day Shoe Deals
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.
Merrell
Moab 3 Mid Waterproof Hiking Boot
A Prime Day MVP, the Moab 3 boot is an all-terrain beast with a reputation for comfort and grip. Lace up and go.
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.
Deer Stags
Bamboo2 Sandal
Go ahead and get your grandpa swag on. These huarache-style sandals are one of our favorite footwear trends right now and they’re best served with billowy pants and a flowy linen shirt.
Early Prime Day Accessory Deals
Timex
Expedition Scout 40mm Watch
Inspired by vintage army watches, this rugged ticker features a lightweight yet durable webbed strap, vintage white dial, 24-hour display, and subtle glow-in-the-dark hands. It ain’t the steepest discount, but a great buy nonetheless.
Seiko
Essentials Watch
Seiko’s Essentials SWR watch incorporates a slew of details that make this model a dead ringer for the Tank, down to the telltale rectangular face, Roman numeral indicators, cabochon crown, and croc-embossed leather strap.
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.
Seiko
SRPD51 Automatic Watch
Once you finally get around to going on that snorkeling trip in the Caribbean, make sure your watch is as dazzling as the crystal blue waters.
Prime Day Clothing Deals FAQ
What should I expect from Amazon Prime Day 2025?
For the first time ever, Amazon Prime Day is slated to be four days long. Except steep cuts on basics (white tees, polos, denim), activewear, sneakers, and outerwear. Brands like Levi’s, Calvin Klein, Dickie’s, and Lacoste tend to unload a lot of inventory. Prime Day is also low-key a great opportunity to snag a new watch, as well as a new cologne.
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.
Do I need to be a Prime member to shop Amazon Prime Day?
Yes, you must be an Amazon Prime member to access Prime Day’s exclusive deals. If you’re not yet a member, you can sign up for a 30-day trial.
How long do the deals last?
For as long as we can remember, Prime Day has been a two-day event. Not this year. In 2025, you’ll have four full days to shop for deals. The deals will begin on July 8 and be live through July 11.
Do other retailers participate in Prime Day?
While there is only one store participating in Amazon Prime Day (uh, Amazon), there are plenty of other retailers that ride off Prime Day’s coattails. There will be plenty of competitive sales worth perusing, and we’ll make sure we surface those deals up for you. For example, Nordstrom’s Anniversary Sale begins on July 12.
