The Best Labor Day Menswear Deals You Can Score for Under $50

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.AmazonBoxers 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.”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.Advertisement - Continue Reading BelowEveryone 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.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.Advertisement - Continue Reading BelowA 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.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.Advertisement - Continue Reading BelowTodd 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.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.Advertisement - Continue Reading BelowCasio 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.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.Advertisement - Continue Reading BelowJust 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.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.Advertisement - Continue Reading BelowIt’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.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.Advertisement - Continue Reading BelowWhether 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.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.Advertisement - Continue Reading BelowIf 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.Can’t decide between a new pair of sneakers or boat shoes? These sleek, under-the-radar Vans offer the best of both worlds.Advertisement - Continue Reading BelowA 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.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.