There is no definitive streetwear story. Anything claiming that title would be unwieldy, contradictory, and too mythologized to be useful. “IYKYK” may be a recent bit of slang, but the principle has undergirded subculture since the beginning — it was never meant for everyone.

Still, there’s no way to talk about fashion without engaging with this scene we’ve retroactively labeled streetwear. No two definitions are the same. Some are so broad and abstract they’re almost religious: Streetwear is self-expression. Some are precise and long-winded, many caveated and discursive (we’ll spare you those). Some folks hate the labeling exercise altogether.

At Highsnobiety, we feel there’s value in taxonomy and narrative — we have a long tradition of white papers, for instance. They are an acknowledgment that, with all the information slung around, sifting and sorting is required to make sense of the historical moment.

To celebrate the fact that Highsnobiety has been around for 20 years, we spoke with 20 designers, brand founders, store owners, and creatives who’ve played a role in the past two decades of personal style. The conversations — available in full on our YouTube page — create collage rather than a linear timeline. There are tangents unremarked upon and important figures left out. Because you’re probably reading this on your phone, feel free to Google anything that needs further context. Or try walking into a nearby store and starting a conversation about one of the moments or people mentioned here. Who knows what you might learn.

All quotes have been edited and condensed for clarity.

For decades, downtown New York has exerted a singular gravitational pull, attracting young iconoclasts, would-be artists, broke social mavens, and connoisseurs of what’s cool and exciting. Clothes, and how they are worn, are always a piece of this. Eventually, the codes and norms of whatever culture is produced south of 14th Street are broadcast more widely, where people who aren’t part of the scene can try to buy in. The gravity draws in the rest of the country. The rest of the world.