Winona was always too cool for school. When Johnny Depp tattooed "Winona Forever" on his arm, how were we to know that it would end up as "Wino Forever"? She exited the eighties as a "Heather" and entered the nineties as the anti-heroine of Generation X, with her iconic role in Reality Bites. Indeed, Miss Ryder was pretty much indistinguishable from the moony, alternative Lelaina from the 1994 movie, which solidified colorful tights, irony, and a disdain for the Gap as hallmarks of an era. As the years passed, Winona went through a series of stages: Academy award nominee, Gwyneth's BFF, notorious shoplifter. Throughout the ups and downs, her sense of style has remained supercool: minimalistic darkness that becomes the vaguely goth raven-haired star of classics like Beetlejuice and Edward Scissorhands. Winona turns 39 today, appropriately close to Halloween. Here's wishing her an amazing day (and the comeback she deserves)! Inspiring Winona looks and gifts to follow!