This story starts all the way back in 1865, when Harvard baseball players started sewing big crimson Hs onto the centers of their sweaters. The demarcation meant they were a star player — and, as such, few had one. Cue the classic jock vs. nerd dynamic.
All joking aside, varsity jackets — a.k.a. “letterman” jackets — became standard issue at the Cambridge-based school a decade later. As cardigans came into the fashion, the big logos moved from the center of the chest to the left, where the letters remain to this day. (That said, some schools put them on the arms.) The bomber-like iteration we all know now didn’t arrive until the 1930s, in synchronicity with the rise of high-school sports. No longer were they reserved for the well-off that went to college; anyone could play football, for example, and thus letter. Hence, the surplus of vintage varsity jackets decades later.
But they haven’t always been this popular. It wasn’t until the ’80s and ’90s that the style found its way into the fashion world. Prior, it served as a wearable trophy, a status symbol: you were a student athlete poised to go pro (or at least collegiate), or at least someone who knew someone like that.
The jacket’s private-school-to-public-school-to-pro-sports-to-pop-culture-to-high-fashion transition didn’t happen fast, though. The varsity’s roots are in prep and ivy culture — remember the Harvard baseball team? By the time hip-hop got ahold of them in the ’80s, Run DMC was borrowing the look from jocks, but they were original to the elites. (Are they one in the same? That’s another debate.)
However, we’d be remiss to overlook the Black men that adapted prep staples to their own personal styles decades earlier. Fashion savant Jason Jules wrote the book, Black Ivy: A Revolt In Style, on this.