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.
Style Notes: Part Audrey Hepburn, part James Dean, this black getup pulls together iconic looks from Hollywood's past. Also, great validation for the all-black outfits we always want to reach for.
Style Notes: Remember when corsets and satin were popular? Winona took them to the next level with this flirty combination.
Style Notes: Never have we wanted a brown suit quite so much as we do right now.
Style Notes: Flapper dresses generally don't look that edgy, but there's something about the snug fit and hair curl that really gets us here.
Style Notes: File under "what to wear to work in 2018." This all-black, tailored Winona look feels even better thanks to her matching belt and raven hair.
Style Notes: Gothic, slightly revealing and with that aforementioned grin in full swing, this is classic Winona-on-a-night-out.
Style Notes: My favourite Ryder look of all time singlehandedly makes leather blazers seem cool again, confirms that band tees aren't naff if you know what you're wearing and shows that perfect-fit jeans are a thing of great wonderment.
Style Notes: Winona can do saccharine sweet too—just see this combination of baby-blue dress, pink handbag and silver shoes. She even carried a rose, in case you didn't catch her drift straight away.
Style Notes: Take a moment to focus on the witchy purple velvet slip dress Winona so expertly paired with a thin black choker necklace.
Style Notes: The socks. The funny travel bag. The expression. The beaten-up shoes. Everything about this airport look makes us thankful a paparazzo was working that day.
Style Notes: Ah, the golden age of Gwyneth and Winona's friendship, where strappy black shoes were the bomb and party skirts were best worn with vests.
Style Notes: Mixing the minx of a tight leather skirt with the demure roll-neck, Winona has always done sexy in her own cool way.
Style Notes: Bet you didn't remember this pink satin extravaganza. Props to the actress for going all-in on the look.
Style Notes: There's that leather jacket again, only this time worn buttoned up, over a miniskirt and with some rather tight black boots we think Alexa Chung would like today.
Looking for more flashback fashion inspiration? Enjoy some of the most memorable '90s fashion moments we all experienced.