Winona Ryder pretty much defined a generation. It all began with a string of iconic cult roles in the late 80s and early 90s–from Heathers to Beetlejuice, Ryder built a reputation portraying the alternative outcast with a distinct, kooky charm. She became the face of the slacker generation, a personification of the awkward, self-conscious, and young Gen-Xer, demonstrated particularly well in Reality Bites—made in 1994, when the “slacker” was at its peak.
This carried over into her fashion choices as well. While other celebrities were gracing the red-carpet in gaudy sequined things and Elnett, Ryder said “hell nah” and wore men’s suit jackets and red lipstick instead. She wore vintage dresses before anyone else was wearing vintage, and on her off-duty days, she’d wear the essential Gen X uniform–a white tee, slightly oversized jeans teamed with a black belt, and a black Moto jacket. Timeless and legendary, this look is still as important today as it was back then and–luckily for you–we’ve re-created it below. You’re welcome.