The Best Prime Day Menswear Deals Are Too Good to Pass Up

Lacoste

Short Sleeved Ribbed Collar Shirt

If there’s one shirt worth picking up on Prime Day, it’s Lacoste’s signature polo, done up in a now-legendary cotton pique fabric that has endeared it to prepsters and punks in equal measure.

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.

Levi’s

Classic Western Shirt

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.

Madewell

Workwear Overshirt

Thanks to Prime Day, you can now underpay for this overshirt. Pair it with some cutoff shorts and leather sandals and you’ve got the ideal summer fit.

Umbro

Checkered Shorts

Mic check, 1, 2, 3, 4 pairs of shorts at this Prime Day price.

Beaudrm

Mesh Football Jersey Shirt

Have we ever heard of Beaudrm? No. Do we like this mesh football jersey and think it’ll absolutely hit during sweltering summer days? Yes.

Eddie Bauer

Ripstop Shorts

The Eddie Bauer Ripstop Shorts are built for whatever summer throws at you—lightweight, tough, and quick-drying. Great for hikes, travel days, or just showing off some thigh.

Columbia

Brewha II Short

The Brewha II Short nails the vintage vibe with a relaxed fit, washed cotton fabric, and old-school cargo pockets. It’s like your favorite ’90s pair, but built better.

Dockers

Relaxed Fit Pleated Comfort Khaki Pants

Dockers’ relaxed fit khakis are soft, roomy, and built with stretch—like your dad’s, but in a good way. The pleated front and British khaki tone keep them easy and classic.

Colortone

Spider Tie Dye T-Shirt

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.

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.

Adidas

3-Stripes Tricot Opem Hem Track Pants

Fulfill your lifelong dream of becoming the swaggy track coach, all from the comfort of your couch.

Red Kap

Industrial Stripe Work Shirt

Union or not, this striped shirt is the right tool for the job, even if that job is just heading to the cafe to be perceived by the local baddies.

Levi’s

Harrington Jacket

The Harrington Jacket from Levi’s is about as classic as it gets—short, sharp, and built to layer. Toss it over a tee or oxford and you’ve got a fit that never misses.

Levi’s

569 Loose Straight Denim Shorts

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.

Wrangler

13MWZ Cowboy Cut Original Fit Jeans

The Wrangler 13MWZ is the real-deal cowboy jean, cut straight from the rodeo circuit and tough enough to ride fence all day. High rise, zero stretch, full yee-haw energy.

Calvin Klein

Cotton Stretch Boxer Briefs (3-Pack)

Polo Ralph Lauren

Classic Fit Woven Cotton Boxers (3-Pack)

For guys who prefer boxers over briefs, Polo Ralph Lauren’s woven boxers are still the gold standard when it comes to price, comfort, and breathability.

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.

Gap

3-Pack Tank Top

The hottest thing you could wear during summer is also the thing that’ll keep you the coolest. This triple-pack of ribbed tanks is simple, classic, and will turn up the heat on every outfit

Champion

Powerblend Open-Bottom Sweatpants

Champion

Reverse Weave Hoodie

From streetwear obsessives to schlubby-stylish celebs to everyday dudes, the iconic Reverse Weave hoodie will forever be a top tier sweatshirt. The hearty cotton-blend fabric and classic cut come together in a way that countless brands are still trying beat.

Comfort Colors

1717 Heavyweight Tee

The Comfort Colors tee is a heavyweight champ—thick, soft, and garment-dyed for that perfectly faded look. It’s the kind of shirt that gets better with every wash and feels like an ol’ favorite out the gate.

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.

Russell Athletic

Relaxed Fit 9″ Shorts

Roomy, breathable, and built to move—these relaxed-fit shorts from Russell are perfect for workouts, grocery runs, or just kicking it around the house.

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.

Russell Athletic

Dri-Power Full Zip Hoodie

A classic is a classic is a classic. The Russell Athletic Dri-Power Full Zip Hoodie nails the basics with soft fleece, moisture-wicking fabric, and an easy fit that goes with everything.

Carhartt

Rain Defender Loose Fit Heavyweight Sweatshirt

Not only does Carhartt’s triple-beefy hoodie defend from rain, it defends from bad outfits.

Havaianas

Flip Flops

New Balance

997 Sneakers

Every generation has its New Balance and for the hip Millennial crowd, it’s the 997.

Puma

Speedcat OG Sneakers

The Puma Speedcat OG launched in ’99, inspired by classic motorsport gear. With its low profile, suede build, and sleek lines, it’s a throwback that’s a worthy addition to any sneaker rotation.

Reebok

Club C Vintage Sneaker

The Reebok Club C is one of the most underrated and understated sneakers out there. But it’s that restraint that makes them just plain cool.

Brooks Brothers

Campus Loafer

Of course Brooks Brothers makes a “Campus” loafer—it practically invented the campus uniform. This one’s sleek, sturdy, and classic enough to make you feel like the big man on campus (again).

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.

Converse

Chuck Taylor All Star High Top Sneakers

Puma

Easy Rider Sneakers

With a seriously cool throwback look and an icy cool colorway, Puma’s Easy Riders are the hidden gem of the sneaker world and you won’t have to worry about other people jacking your style.

Deer Stags

Bamboo2 Sandal

Go ahead and get your grandpa swag on. These huarache-style sandals are best served with billowy pants and a flowy linen shirt.

Nisolo

Huarache Sandals

Our favorite pair of summer-friendly, vacation-prone huaraches are on sale, so you can put those extra bucks toward a couple of tropical cocktails.

Dr. Martens

1461 Soft Toe Oxford Work Shoe

The 1461 Oxford blends the brand’s iconic silhouette with work-ready durability. It’s cushy, slip-resistant, and tough enough for long shifts—but still sharp enough to wear off the clock. A true all-day, everyday shoe.

Dr. Martens

Adrian Loafer

The Adrian combines all the edge of a combat boot with the polish of a dress loafer. Easy to wear, hard to beat.

Chaco

Z/1 Classic Sandal

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

Merrell

Moab 3 Mid Waterproof Hiking Boot

A Prime Day MVP, the Moab 3 boot is an all-terrain beast with a reputation for comfort and grip. Lace up and go.

Keen

Uneek II Slide Sandal

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

Sebago

Classic Dan Loafers

Like dessert, there’s always space for a pair of loafers. And whether you’re a style maven or a regular Joe, these simple penny loafers are the ones you should have.

Oakley

Radar EV Path Rectangular Sunglasses

If you’re serious about performance—or just like looking like it—Oakley’s Radar EVs offer top-tier optics and an unmistakable silhouette.

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.

The North Face

Borealis Laptop Backpack

The North Face Borealis Backpack is built for daily hauls, with a padded laptop sleeve, tons of compartments, and seriously comfy straps. Great for commuting, class, or weekend hikes.

Juli

Sport Sunglasses

Cheap and cheerful, emphasis on both. These sporty shades are the essence of ’90s cool with a sort of JFK Jr. sharpness about them.

Lands’ End

Open Top Canvas Tote Bag

The Lands’ End Open Canvas Tote looks a lot like a certain iconic bag (coughs L.L. Bean) and honestly, it does the trick. Sturdy, roomy, and ready for beach days, errands, or laundry hauls.

Persol

PO3059S Square Sunglasses

Ditch the usual Aviators and grab these Steve McQueen-approved shades instead.

Ray-Ban

RB3016 Clubmaster Square Sunglasses

The Clubmasters are a mid-century modern icon—half-frame, all style. They strike the perfect balance between timeless style and everyday wearability.

Troubadour

Apex Compact Backpack

The Apex Compact Backpack trims the fat without cutting corners. Its slim silhouette keeps a low profile, but still fits your laptop, chargers, and daily carry with ease. Water-resistant, well-padded, and handsome enough to make your other bags jealous.

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.

Oakley

M2 Frame Sunglasses

No longer are Oakley’s sports-designed shades just for pro-level athletes. Pop these on your face and you’ll feel fast and fly AF.

Timex

Expedition Scout 40mm Watch

Inspired by vintage army watches, this rugged ticker features a lightweight yet durable webbed strap, vintage white dial, 24-hour display, and subtle glow-in-the-dark hands. It ain’t the steepest discount, but a great buy nonetheless.

Apple

Watch Series 10

An affordable Apple Watch, this model comes with GPS for enhanced outdoors and sports tracking. It’s crack-resistant, is IP6X-certified dust resistant, and is water resistant up to 50 meters.

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.

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.

Timex

Waterbury Classic Chrono Watch

The Waterbury nails the dress watch basics: clean dial, leather strap, and just enough vintage flair. At 40mm, it’s an easy fit on most wrists—and a no-brainer if you want sharp looks without the splurge.

Seiko

Essentials Watch

Bulova

Lunar Pilot Chronograph Watch

Tissot

PRX Digital Watch