Back in the mid-nineties, my friends and I spent a lot of time in nightclubs dancing to A Tribe Called Quest and Nas. The de facto uniform was baggy Maurice Malone jeans, stout Champion sweats, and anorak pullovers from preppy brands such as Tommy Hilfiger and Nautica. But the most stylish among us wore Polo Ralph Lauren. Color-blocked sportswear met Polo Bear knits, all-over-print shirts, and choice items from the Stadium and P-Wing collections.

Decades later, fashion writers described this aesthetic as a way for nonwhite youths to appropriate the status symbols of blue-blooded Wasps. That’s partly true. Ralph Lauren’s Polo logo is woven into the American image of financial success, and many of us simply wanted to stunt. But there’s another story here about the thread that laces through this country’s clothing history and the complicated, sometimes contradictory essence of the American spirit. Despite its aspirational nature, American style is, at its core, a celebration of the everyday person.

 It’s also—like all style—a form of visual language. Our outfits are not purely about creative expression; they allow us to communicate our identity, aspirations, and values. If you’re a man getting dressed today, you’re confronted with what can be an overwhelming array of choices and style mashups. Figuring out how to communicate within this cacophony can be disorienting. But the process of doing so is much easier when you understand the foundations of American style and how they shape some of the most inventive designers of the moment.

If dress is a social language, then Brooks Brothers gave us our ABC’s. The company introduced ready-made tailoring in 1849, debuted its No. 1 Sack Suit in 1901, and filled American closets with tweed jackets and Shetland knits. Today, we think of this as Old Money style, and it makes sense, as Brooks Brothers dressed upwardly mobile Americans who rose with industrial capitalism. But to understand what those clothes meant at the time, we have to jump across the pond to Britain. At the turn of the twentieth century, British men in high positions, in trades such as finance and law, wore frock coats; working-class clerks and administrators wore lounge suits (what we would consider a business suit today). Brooks Brothers’ version of the lounge suit was even more democratic. Instead of being bespoke and hand-tailored, it was ready-to-wear and featured more machine work than its British counterpart, with a straighter, more utilitarian fit. The message was clear: Americans were outfitting themselves for a new social order. And they were recognizing the ordinary citizen by dressing down, not up.

American style from all across the spectrum. Keep an eye out for Marlon Brando in a white tee, Thelonious Monk inimpeccable tailoring, James Dean and Jodeci with two riffs on denim, Brooks Brothers’ iconic No. 1 Sack Suit, Fab 5 Freddy and LL Cool J (in Polo Ralph Lauren and a signature bucket hat, respectively), and even a few Kennedys.

The impulse flourished over the next century. Americans helped popularize the two-piece suit and oxford-cloth button-down, more relaxed alternatives to the three-piece and starched spread collar. Ivy League students in the fifties and sixties wore sporty tweeds with country cords and penny loafers. Their working-class counterparts took to the five-pocket jeans, white T-shirts, and leather motorcycle jackets that Marlon Brando turned into a rebel pose. From the bell-bottom jeans and floral shirts of hippies to the repurposed utilitarian garments of punk—and, of course, the creation of westernwear—every innovation pushed men’s wardrobes toward the ever more casual.

That spirit shines through in some of the most exciting American designers working today. At Aimé Leon Dore, where guys will line up for a shot at a color-blocked rugby or a crewneck sweater featuring a dog named Buddy, designer Teddy Santis has constructed a world around the youthful street culture of 1994 N.Y.C. Fear of God founder Jerry Lorenzo makes an exceptional topcoat, but he’s built his brand on showing men how to dress it down with sweats and tracksuits. When Willy Chavarria debuted his collaboration with Dickies, he said he thinks the height of elegance is a “clean, pressed pair of Dickies pants worn with a crisp white T-shirt.” The clothes in that collab exaggerate the proportions worn by working-class Chicanos in California, where Chavarria was born. Even Emily Bode, who has now won CFDA Menswear Designer of the Year twice, celebrates American design’s thriftier elements. Jackets and pants with simple silhouettes are constructed with quilting, mending, and patchwork techniques that American women have used since the Revolutionary War.

Jacket ($2,200), cardigan ($850), sweater ($720, on waist), T-shirt ($250), trousers ($690), and shoes ($690) by Bode; Khaki Navy Scuba watch ($845) by Hamilton.

There are contradictions at play here. The brands we’re talking about aren’t cheap. And the preppy clothes that inform so much of American dress owe some of their allure to the implication of privilege born from inherited wealth. Even if the Kennedys weren’t the Windsors, they were part of America’s ruling class. But those contradictions are somehow even more American. This was the tension my friends and I played with when we wore the symbols of success to underground clubs. And it’s the tension that runs through the history of American style, perhaps even into the future.