Calvin Klein’s genre-defining skivvies didn’t earn that moniker off the strength of Marky Mark’s abs alone. The fit, the feel, the ability to imbue their wearer with a high-octane dose of movie-star confidence? We’d consider those pretty formidable strengths, too. Still not convinced? Check our guide to the best underwear for men and circle back here. (We’ll wait.)

Every pair of jeans you’ve ever owned owes a little something to the 501. The fit is straight, the vibe is eternal, and the break-in potential is entirely yours to write. Usually they’ll run you a respectable chunk of change, but right now, they’re in double-up territory.

Much like the Levi’s 501, Lacoste’s most enduring contribution to the fashion canon remains a blueprint for all the polo shirts that came after it. Its claim to fame today is still as strong as it was when René Lacoste himself debuted it on the tennis court. The only difference? In 2026, you can find it in a million different colors—and with Prime shipping.

The Seiko Tank-style watch toes the line between homage and dupe—but this one lands firmly in the former camp. It’s sharp, affordable, and even better if you catch it on sale.

We love obscure, Japanese-made socks as much as the next fashion editor, but hosiery doesn’t have to be expensive to be good. Gold Toe’s have been our go-to multi-buy socks for years not just because they’re always on sale, but because, well, they’re just plain good.

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.

The most low-key hoodie in your closet might also be the hardest-working. This one wicks sweat, holds its shape, and zips up with no drama. Russell’s been in the game for over a century for a reason.

Combining elements of vintage flight jackets and retro workwear coats, this Western-leaning bomber is tough as nails and easy on the eyes. More importantly, it’s exactly what light jacket season calls for—easy to throw on and sharp enough to carry a fit.

Real-deal hikers aren’t the only folks who swear by Merrell’s legendary Moab boots. We love ‘em for their unmatched utility on the mountains as much as we do their commuting ability in the city.

A packable shell is one of those unsung hero pieces—but when it’s PFAS-free and stamped with The North Face’s trail-tested pedigree, you can drop the “unsung” qualifier. Lightweight, weather-ready, and easy to stash when the skies clear, this is the jacket you’ll reach for way more than you think.

Next to, like, an Oxford-cloth button-down, a western-inflected denim shirt should be the most versatile in your closet. And if our trend-detecting technology is calibrated correctly, no denim shirt will enjoy a bigger resurgence this season than Wrangler’s cheap-and-cheery snap-front joint. Sleep on it at your own peril.

Oakley might be known for its wraparound, high-octane frames, but the Holbrooks prove the brand can do low-key just as well. Classic and sporty, throw ’em on with literally anything and call it a day.

Wait a minute—Hermès…on Amazon? Believe it, buddy! Don’t expect to see any of the vaunted French maison’s lusted-after leather goods, but you can snag a bottle of its wildly popular eau de parfum—and on sale, to boot. Thanks to notes of bergamot, grapefruit, vetiver, and amber wood, it’s equal parts woody and bright, and a perennial GQ favorite for that exact reason. In other words, a whiff of spring in every spritz.