Men's Lifestyle August 21, 2026 0 Comments

Unlock Unbeatable Labor Day Menswear Deals That Only the Savviest Shoppers Are Snagging Right Now!

Fall—oh, that bittersweet season when the chill sneaks in, the sun says its early goodbye, and suddenly your carefree, sweaterless evenings seem like a distant memory. But hey, who’s not a sucker for the cozy vibes, football Sundays, and the hunt for that perfect jacket to rock while leaves crunch underfoot? Still, let’s be real—saying farewell to that hard-earned summer tan feels a bit like waving off an old friend. So, here’s a question for you: Why not turn this seasonal blues into a shopping spree victory lap? Labor Day weekend is primo for snagging killer deals that not only upgrade your seasonal wardrobe but give you a sneak peek at next spring and summer essentials—all without burning a hole in your wallet. From Ralph Lauren to Lululemon, the steals are already rolling in, ready to boost your style and your spirits. Curious to see what’s hot and happening? Dive into the best Labor Day menswear deals that’ll have you stepping into fall like a boss. LEARN MORE

5 min read

For some, fall is a bit of a double-edged sword. There’s something heartwarming about the cozy months. You get football, perfect jacket weather, and the holidays inching ever closer. It also means the end of long, sun-drenched days and sweaterless evenings. Kiss that tan you worked on all season goodbye.

If any of this strikes a chord, Labor Day weekend offers the spiritual solution. Yes, that’s getting on the grill and enjoying the last bit of summer, but we’re also talking about shopping. Labor Day is one of the best times of year to upgrade your closet.

Even better, the early Labor Day style deals are really good this year, so you can already start saving on all the stuff you want from brands like Ralph Lauren, Lululemon, and Carhartt. You can use these sales to snag staples for next spring and summer at record-low prices, or to prep your fall wardrobe and get a bit more excited about the change in seasons. Either way, consider it a little mood booster. If you want a cheat sheet, below are the best Labor Day menswear deals to jump on now.

Esquire’s Five Favorite Sales

We’re not the biggest fans of Amazon menswear, but you can get essentials for dirt cheap over there. Levi’s, Lacoste, and any sort of down-range designer is available on markdown. (Note: Levi’s is also having a sale of its own right now, with up to 30 percent off select items, but some of the jean deals are steeper on Amazon.) These are our personal picks.

Lacoste Classic Fit Original L.12.12 Polo

Now 50% Off

Credit: Amazon

Levi’s 505 Regular Fit Jeans

Now 40% Off

Cole Haan Pinch Penny Loafer

Credit: Amazon

Somewhere we do like is Huckberry. We think it’s one of the best places on the internet for Normal Guys to shop at. Ahead of Labor Day, the brand’s sale section is stacked with end-of-summer steals and fresh fall-ready pieces worth stocking up on, from a Carhartt chore coat to our favorite Flint and Tinder western shirt.

Carhartt WIP Warren Chore Coat

Now 30% Off

Rhodes Footwear Western Mule

Now 30% Off

Flint and Tinder Bone Button Western Shirt

Now 20% Off

It’s no secret we’re big Brooks Brothers fans. After a few years in limbo, America’s most important catalog, the brand that’s dressed (almost) every president since 1818, is starting to reclaim some of the territory we think it lost. If you’re into the prep look, there’s nowhere better to score a deal on it—especially now that the brand’s end-of-summer sale has markdowns of up to 60 percent off.

Brooks Brothers Windowpane Sport Coat

Now 40% Off

Credit: Brooks Brothers

Brooks Brothers Stretch Cotton-Oxford Button-Down

Now 58% Off

Credit: Brooks Brothers

Brooks Brothers Lightweight Luxe All-Season Sweater

Now 51% Off

Credit: Brooks Brothers

Gap’s inventory has gotten pretty great in recent years, but not at the expense of its stellar prices. And right now, they almost don’t seem real: for a limited time, save an extra 40 percent off select sale styles, with prices starting at just $12.

Gap AC/DC T-Shirt

Now 70% Off

Credit: Gap

Gap ’90s Double-Knee Carpenter Pants

Now 73% Off

Credit: Gap

Gap Seersucker Shirt

Now 55% Off

Credit: Gap

The Hoka sale is fine. The one really good deal is 20 percent off the Clifton 10, which is a season old now but still beloved here at Esquire. The Challenger 8 trail runner is 20 percent off with limited sizes. The Arahi 8, a trusty daily trainer, is 20 percent off in a slew of neutral colors. And two earth-toned versions of the springy Skyflow are the most steeply discounted at 30 percent off. But chances are you want the Clifton. Here it is.

The Rest of the Sales

For a limited time, Abercrombie is offering up to 30 percent off most of what’s on its site. That translates to 20 pages of discounts on trendy menswear items like hoodies, wide-leg jeans, and graphic tees.

Adidas’s current sale is full of classics. There are Ultraboosts, Spezials, and Gazelles up to 40 percent off in honor of the back-to-school season. Great place to pick up some sneakers.

If high-end, designer clothes are more your thing, you do not want to miss out on Bergdorf’s designer deals. Through Labor Day, take up to 70 percent off select designer brands, including Tom Ford, Brioni, Zegna, and more.

Bloomingdale’s also has some under-the-radar deals on designer and contemporary favorites, including up to 60 percent off on Theory tees, Magnanni loafers, Eton dress shirts, and a handful of On sneakers. Right now, you can score one of our go-to walking shoes, the plush On Cloudmaster Void, for a rare 20 percent off.

Though the edit is somewhat tight, Filson’s outlet section has up to 40 percent off rugged fall essentials like wool shirt jackets, preppy shawl-collar cardigans, and sleek bombers. Don’t miss your chance to score some of the best outerwear around for a fraction of the price.

J. Crew’s end-of-summer sale definitely deserves a scroll. For a limited time, enjoy up to 40 percent off on select styles like lightweight crewneck sweaters and top-rated chinos. We’ve already curated our favorite picks for you right here.

J.Crew Darkest Indigo Navy Red

Now 24% Off

Credit: J.Crew

J.Crew Ludlow Slim-fit suit pant in Japanese cotton chino

Now 31% Off

Credit: J.Crew

J.Crew Vintage-wash cotton pocket T-shirt

Now 38% Off

Credit: J.Crew

If you love Lululemon (honestly, who doesn’t?), you’re going to love shopping the athletic brand’s discounted best-sellers even more. From shorts and tank tops to button-downs and underwear, it’s all happening here.

Mack Weldon never fails to impress us with its simple, impossibly cozy basics. Find major savings on the brand’s beloved boxers, henleys, sweats, and more.

For all your sporty needs, take a peek at Nike’s sale section. There are more than 2,000 markdowns to sift through, and while some of the discounts are pretty slim, dig a little and you’ll find steals like Killshots for nearly 40 percent off.

For everything from office attire to home essentials, Nordstrom has you covered. The retailer’s early Labor Day deals are already selling out fast, so shop ’em before they’re gone.

While Ralph Lauren isn’t technically hosting an official sale right now, must-have polos, quarter-zips, and even select colors of its iconic logo chino cap are way cheaper than normal. If you haven’t perused the brand’s clearance section yet, consider this your wake-up call.

If you still plan on touching grass even when the days get shorter and the weather gets chillier, one, good for you, and two, make sure to check out REI’s outlet section. Arc’teryx shells, The North Face technical pants, and even Patagonia fleeces are 30 percent off or more while supplies last.

We’re never not on the hunt for the best Todd Snyder deals. And while the brand’s Labor Day sale is expected to be phenomenal—we saw an extra 30 percent off sale items last year—the cool polo sweaters and leather flip-flops in its current sale section are worth adding to your cart if you can’t wait until the long weekend.

For basics that know how to ball on a budget, Uniqlo is the obvious answer. In the lead-up to Labor Day, save through August 28 on everything from top-rated clothing to accessories. If you thought the prices were already good, these deals are even better.

Vuori’s sale section is full of best-sellers right now. Everything from the cult-loved Kore shorts to the editor-approved Sunday Joggers, which contributor Gibson Johns dubbed “a fantastic pant that offers immense comfort,” is currently up to half off.