#WinonaForever: 12 Winona Ryder Outfits That Are Still Cool Today

The history books of indie fashion would be nothing without Winona Ryder's style. No matter how cookie-cutter Hollywood might have been around the time she rose to fame in the '90s, this actress never relented in the important quest of remaining true to herself. As is the same story for Winona today, she's always erred on the side of grunge, looking to the wardrobe essentials of beatniks and tomboys instead of glossy starlets.

However, Winona's off-duty and red carpet–duty styles certainly differ. When laid-back and probably reaching into her own closet, she's all oversized tailoring, chunky flats, retro tees and denim. At galas, premieres and award shows, Winona's most enduring looks revolve around elegant, understated '90s gowns worn most commonly with pashminas, a teeny-tiny handbag and her ever-present smirk. We've always had the feeling Winona knows something we don't—is it the secret to effortless style? Quite possibly.