The Best Labor Day Menswear Deals You Can Score for Under $50
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You spent most of your summer paychecks traveling , drinking , and living well . Does that mean you shouldn't be allowed to buy some new clothes to get you excited for the drop in temperature? We don't think so. To be clear, we're not a financial advice magazine, but we can also say that you should (maybe) not put clothing purchases on a credit card you can't pay off, God forbid Klarna it. If you're feeling the need for a little fall menswear but have to stretch the budget, we found you plenty of dirt-cheap picks.
The under-$50 Labor Day menswear basics I unearthed check all the boxes: They're things you likely already need. They are top performers in their categories (meaning Esquire has shouted them out previously ). And, they look good. Think a pack of sleek Hanes tees commerce editor Luke Guillory calls "the only blank tee he owns," some classic Calvin Klein boxers , and the pair of rear-hugging Wranglers Guillory has also sworn by for years . I even found some retro Reeboks and a sharp Rag & Bone polo for less than a General Grant right now.
To be fair, a few of these finds, albeit generously discounted, were already under $50. Most, however, would be hard to find this cheap at any other time of year—at least at this point until Black Friday, when these specific styles may already be sold out.
All that to say, scroll down to shop these under-$50 Labor Day menswear gems before it's too late. Grab one or many—I'm certainly not one to judge.
1) Calvin klein Calvin Klein Men's Cotton Classics 3-Pack Boxer Brief,
Boxers are inarguably a universal wardrobe staple—yes, even for the guy who occasionally dabbles in going commando. For the boxer-briefs man, these classic Calvin Kleins are a must. In fact, if you only buy one thing from this list, we'd say make it this three-pack.
"These cotton boxer briefs aren't just hassle-free; they are supremely comfortable," wrote associate commerce editor Bryn Gelbart. "I have plenty of space down there but with all the snug structure I go to boxer briefs for. Same goes for the elastic, which hits that perfect comfort level—staying up effortlessly while never feeling too tight."
2) Hanes Beefy-T (Pack of 2)
When it comes to white tees, it's hard to beat the quality-to-price ratio of a classic Hanes Beefy. "No one, here or abroad, is gonna come up with anything better than [this]," says Guillory, who praises its "impeccable fit." And right now, you can score a two-pack on Amazon for essentially the price of two lattes.
3) Wrangler Cowboy Cut Original Fit Jean
Everyone could use a pair of Wrangler Cowboy Cuts, in our opinion. They nail that classic Americana, straight-cut look, with a super-flattering fit that works just as well with sneakers as it does with—yes—a pair of cowboy boots.
4) Levi's 578 Baggy Fit Jean
Or maybe you're looking for a pair of baggy jeans to channel that downtown-cool aesthetic. Levi's best-selling 578s won't steer you wrong.
5) Reebok Club C Grounds Sneakers
A low-profile retro sneaker never goes out of style—and is the kind of shoe just about any guy can pull off. This version of Reebok's iconic court-inspired Club C comes in a versatile black-and-white suede finish and can be yours for essentially $50.
6) Vuori Clothing Sunday Performance Jogger
Let's face it: you're about to spend a lot more time indoors. Make sure your cozy lineup is up to snuff with a pair of Vuori's editor-loved Sunday joggers, featuring four-way stretch, ultra-soft moisture-wicking fabric, and multiple zippered pockets.
7) Todd Snyder Foundation Pocket Sweatshirt
Todd Snyder's sale section currently only has a few items under $50—mostly tees, caps, and boxers—but this sleek sweatshirt is a rare exception. Made with soft Portuguese cotton terry, it balances sporty raglan sleeves with a fitted silhouette and Oxford-inspired front pocket for a more elevated feel that'll even complement chinos and loafers.
8) Rag & Bone Men's Classic Flame Polo Shirt
Can't resist a steep designer discount? Right now, Bergdorf Goodman is offering an additional 25 percent off clearance items, bringing this Rag & Bone polo down to just $49. Somehow, every size is still in stock—but once word gets out, we have a feeling that won't last long.
9) Casio MTP-VD01D-1BV Men's Enticer Analog Watch
Casio has long been one of our go-tos for reliable watches that won't break the bank . Case in point: This hearty stainless steel watch is perfect for daily wear and will fool everyone into thinking you spent far more than $45.
10) adidas Athletic Cushioned Low Cut Socks (6-Pair)
And while you're perusing Amazon's under-$50 Labor Day menswear deals, you might as well add some socks to your cart. Offered in a pack of six, these versatile, low-cut Adidas socks are cushioned for maximum comfort.
11) Abercrombie & Fitch 51mm Round Sunglasses
Just because the days are getting shorter doesn't mean you won't need some sunnies. Grab an extra pair—or replace the ones you lost or damaged during your summer shenanigans—with these square Abercrombie frames, now half off.
12) Carhartt Iconic K87 Pocket T-Shirt
For a heavyweight tee with a little extra pizazz, it doesn't get much better than Carhartt's best-selling pocket tee . It's got that rugged-cool look, is insanely durable, and is now at its lowest price of the year on Amazon in this edgy sleet gray color.
13) Brooks Brothers Stretch Cotton Non-Iron Oxford Polo Button Down
It's safe to say that Brooks Brothers button-ups are in a league of their own. Thanks to the heritage brand's special savings event, a handful of its already-discounted styles—from dressy to sporty to casual, you name it—are marked down even further to less than $50.
14) Gap Classic Icon Denim Jacket
A denim jacket is the perfect midweight layer to throw on for fickle in-between temperatures. It doesn't hurt that this streamlined, faded-wash Gap style looks right in line with what we saw on the fall/winter 2026 runways.
15) Nike Downshifter 14 Road Running Shoes
Whether you're looking for your first pair of running shoes or are simply on a budget, Nike's Downshifter is a solid choice. You can currently snag it in four colorways on the brand's site for just shy of $50.
16) Lululemon Pace Breaker Linerless Short 7
And to go with said running shoes, consider Lululemon's Esquire-loved Pace Breaker Shorts , which are super lightweight and breathable to help you kick your workouts into high gear. They're part of a fresh batch in Lululemon's "We Made Too Much" section, alongside several other under-$50 finds—so you can refresh your entire workout drawer in one go.
17) Columbia Trailborne Wind Jacket
If you plan on hitting the trails this fall, you're definitely going to need a solid windbreaker. This lightweight Columbia favorite is also water-repellent, in case you get caught in an unexpected shower.
18) Vans 2-Eyelet Boat Shoe
Can't decide between a new pair of sneakers or boat shoes? These sleek, under-the-radar Vans offer the best of both worlds.
19) Mack Weldon Warmknit Waffle Henley
A super-soft, bicep-accentuating henley that basically doubles as a sweater? This fitted waffle-knit pick from Mack Weldon, featuring insulating Thermolite technology, is an easy add to cart.
20) Lands' End Glove Leather Belt
A nice leather belt can get pretty spendy, but it doesn't have to be. Miraculously, this Lands' End staple—with its vegetable-tanned leather, smooth stitching, and just-right width—is on sale for under $50 at Nordstrom.
21) Madewell Lightweight Flannel Button-Up Shirt
In honor of the holiday, Madewell is offering an extra 30 percent off sale styles with code LABORDAYWEEKEND, and the selection is pretty stellar. One of my favorite finds is this quintessential brushed plaid flannel, which I'd call an instant outfit maker.
22) Dickies Original 874 Work Pants
Working in an office where casual Fridays don't exist requires a pretty robust rotation of work pants—or means you're constantly doing laundry, but who wants that? Dickies' classic 874 style is still the best out there for the price and is currently even more affordable than usual on Amazon, with the black pair marked down to just $20. Read our full review here to learn more about what makes them so great, then stock up on a pair—or two—before the deal runs out.
23) Ribbed Shawl-Collar Sweater
There's something so sophisticated about a shawl-collar sweater . It's the kind of cold-weather layer we can easily imagine paired with a set of golf clubs—or a cigar and a glass of brandy. Style it with some light-wash jeans and chunky boots, however, and you can take the look from preppy to laidback-chic, if that's more your vibe.
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