The Early Prime Day Clothing Deals Confirm Amazon Is Back to Its Old Tricks

September 22, 2025

With a fall Prime Day barreling through in October, these early deals are a taste of what’s to come.

September 22, 2025

On sale menswear products from Amazon on a bright gradient background.
Photos: Amazon; Collage: Mari Herrema

All products featured on GQ are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.

The year’s not done with Prime Day just yet. Prime Big Deal Days—the second major sales event from Amazon this year—lands October 7-8, and it’s a two-day gated sale for Prime members. Think of it as a pre-holiday warm-up: preposterously great discounts across fashion, tech, home, and more, timed perfectly to get a jump on your gift list (or finally refresh your underwear drawer).

The firehose of markdowns can feel like a lot, but that’s where your friendly neighborhood shopping desk earns its keep. The GQ Recommends team spends all year shopping the Everything Store, and we know a good deal (and a bad one) when we see it. We’re already tracking early drops and and everything you need to know about the event, and once Amazon’s big sale bonanza officially kicks off, we’ll be updating this page with the only deals that matter.

10 Early Prime Day Clothing Deals to Score Today

The Heavyweight Champ
Hanes BeefyT T-shirt (2-Pack)

See the deal

The Iconic Undies
Calvin Klein Cotton Stretch Boxer Briefs (3-Pack)

See the deal

The Original Blue Jean
Levi’s 501 Original Fit Jeans

See the deal

What should I expect from 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.


Early Prime Day Deals on Our Radar

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.

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.

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.

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.

Seiko

Essentials Watch

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.

Carhartt

East West Tote Bag

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

Hanes

Cotton Tank Undershirts (6-Pack)

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.

Champion

Powerblend Open-Bottom Sweatpants

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

Goldtoe

Crew Socks (6-Pack)

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.

Ray-Ban

Caravan Square Sunglasses

The Ray-Ban Caravan is a slept-on classic—clean, squared-off, and a little more low-key than the Wayfarer or Aviator. If you want timeless frames that not everyone’s already wearing, start here.