Best October Prime Day Clothing Deals: Big Savings on Menswear

Almost as classic as their beloved blue jeans, the Levi’s western shirt is an instant way to add a ton of swagger to every outfit.

Delivered to you faster than Steve McQueen barrelling through San Francisco.

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

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.

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.

Cowboy or not, Wrangler’s jeans will look great on anyone whether you know how to ride a horse or not.

Tap into your innner sporty spice.

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

These shoes have that big dad energy.

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.

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.

If the boat shoe craze has you intrigued but you can’t fully dive in, try out these moccasin lace-ups instead.

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

The cool crunchy sandals you’ve seen on your avid hiking friends and in extremely stylish Japanese fashion circles.

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

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.

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.

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

From the office to the…hiking trail? Theoretically, yes, these dressy lug-soled oxfords can do both.

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.

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.

The go-to shoe for any important event.

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

Your next PR is coming sooner than you think.

Your wrist will never look more handsome than this, especially not for this price.

That face is a sight for sore eyes. Those gorgeous slender hands move so smoothly. And that soft tick is music to our ears. You know we’re talking about a watch, right?

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.

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

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.

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

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.

There’s beauty in simplicity, and Casio’s no-frills resin watch is the dictionary definition of simple.

No, your crew socks will not work with your wedding suit.

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.

Franky, folks, your trunks deserve a break.

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

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.

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.

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.

Handsome Italian leather, classic design, and top-notch craftsmanship—with a discount, to boot.

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

Channel your inner Shoehei Ohtani and turn your fits into a grand slam.

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.

The perfect jacket for attending the Oasis concert or your Taxi Driver Halloween costume.

Who needs an umbrella when rain jackets look this good?

This is what fall was made for.

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.

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

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

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.

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.

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.