The 50 Best October Prime Day Clothing Deals 2024 Still Kicking Around

One of the most iconic work jackets there is, at a price that doesn’t make your wallet work all that hard.

Hey, our buddy (this flannel) thinks you’re (those jeans) are cute. Mind if he introduces himself?

These shoes have that big dad energy.

Tap into your innner sporty spice.

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.

There are greater lessons to learn from Brokeback Mountain, of course, but one of them is to get yourself a stylish sherpa-lined jacket.

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

Texture-rich corduroy in a classic straight-leg fit? What did your legs do to deserve such fine treatment?

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.

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

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.

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.

One of the greatest sneakers of all time, now at at an all-time low price.

You don’t have to live in a city with bodegas to rock these iconic boots. Pair the one and only Timberland boot with baggy jeans and a big puffer for maximum effect.

Step into the season with a proper pair of cowboy boots to give every outfit that much needed southern twang.

Your next PR is coming sooner than you think.

These swaggy Dr. Martens mules have a clear message to send: Watch your back, Birkenstock.

There’s no such thing as bad weather—just bad boots.

An all-time great of the hiking world, these Merrell Moabs are built to handle more than you have the stomach for.

Adventure, we’re told, is out there. Make sure you don’t lost track of time chasing it.

When folks (most of them annoying) talk about the “enduring design language of Scandinavian minimalism”, this is precisely what they mean. Are they right? Sure. Doesn’t stop them from being annoying.

At around 20 bucks full price, Armitron’s legendarily-tough chronograph is always a great buy. At around $13, you’ll need legendarily-tough resolve not to.

If the liquid metal cop from *Terminator 2* wore a watch, it would be undoubtedly be this.

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.

With this slick ticker on your wrist, the only thing you’ll have to pilot are first-class fits.

Rugged nylon strap, handsome French-vanilla face, clean lines throughout: Now that’s one hell of a way to spend your weekend.

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.

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.

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?

Caught up in the crew vs. ankle socks debate? Don’t be. The answer will forever and always be crew socks.

Behind every great pair of tough-wearing boots is a cush pair of warm boot socks.

The easiest way to add some heat to your fits is a delicious waffle-knit tee.

These surprisingly soft PJs will make your 8 hours of sleep feel like 10.

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.

Now this is a shady deal we can absolutely get behind.

Walking out without any jewelry is a lot like cooking a meal without any salt. Remember that.

A jeans’ best friend is a really good leather belt.

Tis the season to swaddle yourself in head-to-toe cashmere.

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

It’s a shirt! It’s a jacket! It’s a shacket perfect hybrid layer for the fall.

One of the best deals on a leather jacket even at full price, Landing Leathers’ classic bomber jackets are high-flying style.

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.

This is what fall was made for.

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.

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.