10 American Menswear Essentials That Will Literally Never Go Out of Style

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While denim is it's own subgenre within the huge expanse that is “Americana,” Levi's 501 is the first and foremost. Effectively the definition of Americana, Levi's 501 jeans not only have over a century of use, but are one of the most exported U.S.' style symbols. From cowboys to school children, nearly every person in and out of the 50 states has donned a pair at some point in their lives. Even if you haven't worn a pair jeans with the signature red tab, you've likely worn one of the 501's descendants, and there's no doubt the classic has set the standard for today's five-pocket jean. From the selvedge hem, to the straight leg, It's as Americana as apple pie.

Ralph Lauren is the United States' greatest living designer. There, we said it. No man has been able to establish a lifestyle empire that comes close to resembling that established by Ralph "The Gawd" Lauren himself. One of his most crowning achievements? The Polo oxford. His polo player-adorned oxford cloth shirt combines the Ivy League classic with one of the most globally recognized logos of all time. Even if you're not who needs to dress up on a regular basis, you can safely assume that most guys have at least one of these buttondowns in their closets.

Like several of the other titans on this list, Schott's Perfecto leather jacket isn't just here for history's sake, it's functional qualities are as long as the jacket's time in popular culture. From Marlon Brando in “The Wild Ones” to The Ramones and New York's CBGB (R.I.P.), the Schott Perfecto isn't just a staple of American industry, but also a symbol of NYC. Maybe that's why a fellow New York counter-culture stalwart, Supreme, has collaborated on their own version of the classic Pefecto. There's something distinctly American about the zipped up, black leather biker jacket—it's like watching a bald eagle soar over the Grand Canyon.

While Chuck Taylors may look a little sparse sat next to a pair of teched-out Nikes, you cannot deny the history, and universal appeal of Converse's Chuck Taylor sneaker. It's not just that these come in basically every color under the sun, it's that their minimal design makes them unbelievably easy to wear with everything—from jeans to a two-button suit. Starting as one of the first athlete-sponsored shoes, the sneaker went from basketball clinics, to becoming the official sneaker of American soliders during World War II. By the time the 60's rolled around, the shoe was everywhere from students to Olympic basketball games. Whether in the classic black or white, or in a reinterpreted pair, in today's world, it's hard not to see a pair of Chucks when you step outside.

What could be said that hasn't already? Without a doubt, every sunglasses producer has reinterpreted (or straight up copied) this silhouette from Ray-Ban. The classic shape—something between and square and rounded frame—is simultaneously hard to describe, but immediately recognizable. The style was born out of the '60s, rose again in the '80s, and has officially secured its timeless status for the guy of today, being the default shape for nearly every single sunglasses label. Sure, you could argue the Aviator frame has just as much power (and you wouldn't be wrong), but you have to admit: when someone mentions their “Ray-Bans,” you can bet they're talking about their Wayfarer frames.

There's something to be said for the king of basics. While Hanes isn't the only manufacturer of plain, white, packaged tees, there's something to be said about the company's ability to become the brand name in basics. When you have cosigns from both Michael Jordan and Supreme, you have to be doing something right.

Meant for cold and wet Maine weather, L.L. Bean's duck boots aren't just the brand's signature product, but it's also the subject of a giant sculpture out front of the brand's Freeport, Maine factory store. The boot, known for a brown leather upper, black rubber midsole, and chain-patterned sole make it one of the hardiest boots available—and truly waterproof. While the boot is over 100 years old (and still in production under L.L. Bean's watch in Maine), it's just as relevant today, with online orders reminding buyers that the boot is in “limited supply.” Hard to beat what's literally a handmade-American classic.

The denim jacket has a history that spans centuries, but for the modern man, denim jackets begin and end with the Levi's trucker. The jacket was next evolution following its predecessors, the Type I, and Type II Levi's denim jackets—ultimately yielding the Type III (otherwise known as the “trucker jacket”) in 1962. While denim jackets were always attached to hardworking individuals via centuries-old indigo chorecoats, the introduction of the Levi's Type III jacket was the beginning of a completely modern denim jacket. Shedding much of the decidedly unnecessary features of earlier model types, the trucker jacket is characterized by a 14 oz. preshrunk denim body, and two chest pockets. It's been the de facto choice of cowboys and cool kids ever since.

Bomber jackets didn't just start with the MA-1, but by the time the bomber jacket hit non-military closets post-World War II, it had become something not unlike Alpha Industries classic surplus-style model. With the classic nylon outer and knit details made the jacket as functional for civilians as it was airplane pilots. It's a practically designed three-season piece of outerwear that is an American classic—that's happened to gain a massive following all over the world. While the truly authentic bombers run in midnight blue or sage green, going with a more traditional fit (bigger sleeves, and cropped-waist) isn't the only option. Today, whether you're looking for a jacket that's had redesigns from American streetwear brands to European fashion labels, it's never been easier to find an MA-1.

Chances are, if you've ever worked a dead-end retail/fast-food job, then you've seen (or worn) a pair of Dickies. But it's not just first jobs; skaters too, have their own history with the workwear classic. The brand's mainstay, the 874, is so popular, that it's one of the only things Dickies has “guaranteed in stock.” As a straight leg chino that comes in more colors than you can count on two hands, it's a no frills trouser works as hard as those who wear it—and what's more American than that?