For a woman who's made a career out of playing the alienated outsider, Winona Ryder sure knows how to stay Ms. Popular in Hollywood. Despite her very public indiscretion (more on that later), the actress has an unshakeable staying power and a unique brand of charisma that's kept the subversive star in favor.
Winona's relatively bohemian upbringing (her godfather was Dr. Timothy Leary) seems like quite a fitting start to an acting career full of free-thinking, empathetic characters with equally as open-minded senses of style. In 1988, we saw Winona go totally goth for her breakout role in Tim Burton's "Beetlejuice" followed by her turn as a quintessential '80s protagonist in "Heathers." Fortunately for Winona, her grunge-meets-glam style seemed to align perfectly with youth culture at the time. (It didn't hurt that she was often photographed alongside then-boyfriend and "Edward Scissorhands" co-star Johnny Depp.)
The '90s saw the petite actress crop her hair into one of the most covetable pixies we've seen since Edie Segwick's mod 'do. Winona continued to ride the lost soul-wave in films like "Reality Bites" and "Girl, Interrupted," but the millenium didn't prove to be as kind to the star as previous years. In 2001, she was caught stealing over $5,000 worth of merchandise from a Saks Fifth Avenue in California. Although she went on to get her charges dropped from a felony to a misdemeanor, this shoplifting incident caused Winona to take some space from the industry.
Winona's hiatus ended in 2006, and the brunette went on to make appearances in "Black Swan" and Tim Burton's 2012 film "Frankenweenie." Scandal aside, Ms. Ryder certainly has the personality, beauty and talent to stay a prominent figure in both the acting and style worlds. We don't care if Johnny Depp changed his tattoo, "Winona Forever" will always be our slogan.
In honor of Winona Ryder's 41st birthday on October 29th, we're taking a comprehensive look at her style. Check out her evolution and tell us which Winona era is your favorite!