Yo, Can Somebody Tell the Prime Day Menswear Deals to Log Off? (2024)

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.

What better way to canonball into summer than with a pair of classic navy swim trunks?

If Tony Soprano invested in a grip of these, he wouldn't have sweated the details as much.

Whether you have a surfboard or, hell, a body of water close to you, don't limit these H2O-friendly shorts to wet situations.

Nothing in this world is really "perfect", but there are plenty of things that are really, really close. With the Prime Day discount, these shorts are near immaculate.

The coolest summer shirts actually look like your grandmother's dinner table.

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

So much damn pocket space your filing cabinet just blushed.

Hamilton's an American horological icon that's been on the wrists of countless stylish dudes and handfuls of badass guys (Bond, James Bond). This gold-case square number is one showstopping timepiece that'll get you into any fancy restaurant without a reservation.

Rugged nylon strap, handsome French vanilla watch face, and clean lines throughout. Now that’s one hell of a way to spend your time on the weekend.

People of the world: Stripe up your life!

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.

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.

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

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

Minimalist wallet, maximalist savings.

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.

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.

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

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.

Yeeeeeeeeeeee hawwwwww!

If you're looking for a pair of loose jeans that aren't full-on baggy, the 550 is a great place to start—even better when they're 65% off and only $24.

There's no reason you should be able to take 49% off one of the best wide(r) leg jeans out there, but let's not fight a good thing.

If you've invested in some boots, you should have some bootcut jeans—especially when they'll only run you $40.

The original rockstar jeans, discounted a whole 53%.

Add some zest to your everyday basics with this hand-dyed tie-dye T-shirt. At nearly 40% off, we recommend stocking up on your favorite colors.

Tis the summer of baggy denim shorts and there are few out there offering as much as Levi's does. This 569 cut is very roomy and comes in a gang of great washes.

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.

This is the summer that your thighs go full-on Eddie Bauer edition.

Fresh, breezy linen in an even fresher camp collar style. Don’t forget to peep Amazon’s Shopbop section where you’ll find handfuls of higher-end brands like Vince, Corridor, and Illesteva.

While we love Wrangler's boot cut jeans, these relaxed-fit cargos are a great choice for anyone looking for a pair that can hold up to a honest day's work.

The original luxury sneaker, Tretorn's preppy classic tennis sneaker is still as fresh and clean today as it was when it first hit the clay in the 1967.

On's ascent as one of the biggest disruptors in the athletic brand space is astounding...and for good reason.

Add a bit of funk to your mixtape.

Kick your cardio into high gear and lace up these pavement-pounding trainers.

Merrell's Hydro Mocs are a cheat code for those who wanna go shoeless. They're breathable, lightweight, and at over 30% off, a bonafide steal.

You won't find the Samba OGs on sale during Prime Day, but the Classics, with their extended tongue, are the next best thing.

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

Wonderfully weird and freaky cool, Keen’s hiking-enabled webbed slides offer tons of support, traction, and style on and off the trails.

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

Crocs are cool now. Thanks to Prime Day, they're also ridiculously cheap.

Green bubbles unite! Google's Pixel watch has a universe of snazzy features from e-mail to music to fitness monitoring and more, all within the Android sphere.

Solar-powered watch? That’s a modern-day sundial complete with bluetooth connectivity, radio-controlled time adjustment, 200-meter water resistance, and much more.

There's beauty in simplicity and this no-frills resin watch from Timex is the dictionary definition of simple.

Well, this is one surefire way to make you look and feel 10x more handsome.

Fancy cigars, sips of rare whiskey, and leather-bound books are all par for the course for the distinguished gentleman. A really expensive watch? Not necessarily.

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

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 might only be room for 20 drivers in Formula 1, but your dream of snagging a watch just as sexy as an F1 car can come true.

Orient's watches have always looked (and acted) way more expensive than they actually are. We present you exhibit A.

Finally, a watch that looks like it's a transformer whenever you're not checking the time.

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.

Goldtoe doesn't just make some of the best casual crew socks around, they also do some great office-appropriate dress socks to match your suit.

At just 50% off, these classic Ray-Bans are comfortably under $100 and that's something we don't get to say very often.

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.

Whether you've got travel plans or not, this water-resistant tote can take on any scenario from commuting to the office to absconding to Oslo.

Behold, a belt that has it all: woven leather, silver-toned hardware, a western flair, and a damned good price tag to boot.