Last week it was announced that Winona Ryder was coming back in a big way—as the star of Rag & Bone’s fall/winter 2014 campaign. The doe-eyed actress first hit the Hollywood scene in 1986’s Lucas and has gone on to star in cult film classics like HeathersEdward Scissorhands, and Reality Bites, as well as critically acclaimed movies including Girl, Interrupted and Black Swan. And along the way, she made waves with her evolving sartorial choices. As the ultimate ’90s It girl, Ryder initially caught the public’s attention with her tomboyish style, but her uniquely chic taste kept us coming back for more.

Though Ryder clearly prefers to wear black on the red carpet, she infuses her wardrobe with a variety of styles in the color. From girly to goth to grunge, the star has tried every look in the book. Never one to ignore a trend, Ryder has rocked oversized blazers, velvet slip dresses, leather jackets, LBDs, headbands, dazzling gowns, and menswear-inspired pieces over the years. A pop culture icon in her own right, the actress has worn some of fashion’s biggest names including Dolce & Gabbana, Marc Jacobs, Christian Dior, and Givenchy, all while dating some of Hollywood’s hottest leading men, like Rob Lowe, Johnny Depp (who can forget his infamous “Winona Forever” tattoo?), and Matt Damon.

Take a trip down memory lane and check out Winona Ryder’s 27 most memorable fashion moments in our gallery!