Wake up, folks, Prime Day clothing deals are running amok. Wait, didn’t we just have Amazon Prime Day? We sure did. But, very technically speaking, the deals you’re seeing are actually from what Amazon is calling “Prime Big Deal Days,” which just kicked off today.
Prime Big Deal Days is a full-blown bonanza of deals and discounts on everything you think of—tech deals, kitchen deals, watch deals, and so much more. Just like Prime Day, Amazon’s doling out a mountain of discounts for just 48 hours, and we’ll be working around the clock to bring you the latest and greatest of what Amazon has to offer.
Amazon isn’t exactly the menswear haven most fashion guys turn to, but if you know how to shop it, you can make out like a certified style icon with a much smaller budget. But 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. Go forth and get yourself a good deal.
For every other worthwhile bargain on our radar, head over to our massive list of the best Prime Big Deals Day sales so far. To receive all our shopping intel going forward, subscribe to the GQ Recommends newsletter.
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.
Dickies
Insulated Eisenhower Front-Zip Jacket
One of the most iconic work jackets there is, at a price that doesn’t make your wallet work all that hard.
Dockers
Relaxed Fit Comfort Pants
This may very well be the epitome of “business casual” pants—a pleated relaxed-fit pant that’ll pair well with any day of the week.
Brooks Brothers
Non-Iron Long Sleeve Button Down Stretch Oxford Sport Shirt
We might not have button-down shirts if it weren’t for Brooks Brothers. Over a century since its invention and they’re still among the best to do it.
Wrangler
13MWZ Cowboy Cut Original Fit Jean
Cowboy or not, Wrangler’s jeans will look great on anyone whether you know how to ride a horse or not.
Adidas
Essentials Warm-up Open Hem 3-stripes Tracksuit Bottoms
Tap into your innner sporty spice.
Lacoste
Short Sleeve Classic Pique Polo Shirt
Pendleton
Long Sleeve Wyatt Shirt
Hey, our buddy (this flannel) thinks you’re (those jeans) are cute. Mind if he introduces himself?
New Balance
997H V1 Sneaker
Attention all Cool Dads: your new pair of sneakers is on sale.
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.
Gap
Long Sleeve Oxford Button Down Shirt
The ultimate do-it-all shirt is undoubtedly a striped button-up shirt. From everyday hangs to fancy dates to office attire, this one from Gap will adapt seamlessly to any occasion.
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.
Best 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.
Blundstone
Original 500 Series Boots
There’s no such thing as bad weather—just bad boots.
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.
Converse
Chuck 70 Low Sneakers
One of the greatest sneakers of all time, now at at an all-time low price.
Ugg
Gatson Chelsea Boot
Ugg may be known for its supremely fuzzy boots and slippers, but when you’ve got to go outside in less-than-cozy weather, they’ve still got you covered.
Merrell
Moab 3 Hiking Shoe
An all-time great of the hiking world, these Merrell Moabs are built to handle more than you have the stomach for.
Allen Edmonds
Park Avenue Cap Toe Lace Up Leather Oxford
From the office to the…hiking trail? Theoretically, yes, these dressy lug-soled oxfords can do both.
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.
Allen Edmonds
Classic Oxford Shoes
The go-to shoe for any important event.
Sperry
Authentic Originals Boat Shoes
Boat shoes are undeniably one of the most controversial trends of the summer. Why not spark some conversation?
Asics
Gel-Kayano 30 Running Shoes
Your next PR is coming sooner than you think.
Best 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
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.
Bulova
Archive Series Lunar Pilot 6-Hand Chronograph Watch
With this slick ticker on your wrist, the only thing you’ll have to pilot are first-class fits.
Casio
GM-B2100D-1A Watch
If the liquid metal cop from *Terminator 2* wore a watch, it would be undoubtedly be this.
Citizen
Eco-Drive Promaster Dive Fugu Watch
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 face, clean lines throughout: Now that’s one hell of a way to spend your 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.
Best 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.
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)
Franky, folks, your trunks deserve a break.
Heavyweight Cotton Long Sleeve Thermal Top
The easiest way to add some heat to your fits is a delicious waffle-knit tee.
Ultimate Tagless Tank (7-Pack)
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.
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?
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.
Best 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.
Ashford Ridge
Full Hide Leather Belt
A jeans’ best friend is a really good leather belt.
Oakley
Whisker Oval Sunglasses
Channel your inner Shoehei Ohtani and turn your fits into a grand slam.
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.
Ray-Ban
Orion Square Sunglasses
Now this is a shady deal we can absolutely get behind.
Best 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.
Barbour
Liddesdale Quilted Jacket
This is what fall was made for.
Brooks Brothers
Corduroy Trucker Jacket
Brooks Brothers may be known for their classic American tailoring and preppy styles, but they can also get down into the more rough-and-tumble side of menswear.
A-2 Leather Flight Bomber Jacket
One of the best deals on a leather jacket even at full price, Landing Leathers’ classic bomber jackets are high-flying style.
Columbia
Powder Jacket
Puff, puff, do not pass up this puffer jacket.
Adidas
Essentials Warm-Up 3-Stripes Track Top
Ted Lasso will never return (or will it?), 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 EST 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.
When she's not writing about lifestyle, books, sports, education, or tech for Ris News-Digital, Alyce Monroe is spending time with her family, reading, and working on her golf game. She's also a big fan of Harry Potter and loves to travel to places like Italy and Japan!