The Stunning Hair Transformation Of Winona Ryder

Among performers with long-running careers, there seem to be two camps: those who stick close to their signature look, and those who freely change with the times. We've seen some pretty phenomenal celebrity glow-ups and beauty evolutions over the years, including the many ways our favorite '90s A-listers have worn their hair. Just look at the stunning hair transformation of Jennifer Aniston, who's enjoyed a varied career (with varied hairstyles) since her starring role in "Friends."

The same could be said for eccentric leading lady and cult icon Winona Ryder. Ryder's gothy, breakout performance in "Beetlejuice" in 1988 cemented her place in cinema history and set her on track to be a '90s darling, but the actor hasn't let that period define her. Instead, Ryder has expanded her legacy with a broad field of roles, styles, and, yes, haircuts. From the early days of "Heathers" to her renaissance in "Stranger Things," let's take a look back at Ryder's storied career — and all the stunning hairstyles she's sported along the way.

Winona Ryder kicked off her acting career in the late 1980s, but the early '90s solidified her spot among Hollywood legends. Between filming now-classics like "Edward Scissorhands," "Reality Bites," and "Little Women," Ryder was a regular on red carpets and in magazine spreads. With so much visibility, it's no wonder that she quickly became synonymous with trends of the age, including the decade's oh-so-popular bixie. Ryder showed off this trendy cut in a 1990 photoshoot, pairing the style with a rich, chestnut hair color. Swooping her hair back gave the short silhouette a casual and playful tone, showing a softer side to the often grunge-inspired actor.

Ryder continued to embody '90s trends by flaunting a dark bixie in the 1995 film "How to Make an American Quilt." Here, the style took on a moodier feel, worn with a side part and a dark, cool-toned brown that emphasized Ryder's expressive eyes. We love the surprising versatility of this look and its continued relevance. That's right, with everything '90s rising in popularity again, you can once again slay in a bixie cut — as long as you know how to style it.

The move into the late 1990s didn't slow down Winona Ryder at all. If anything, her career continued to gather steam with huge performances in films like "The Crucible," "Alien Resurrection," and "Girl Interrupted." Meanwhile, Ryder also delivered some of our favorite celebrity hair moments from the '90s, especially when she entered her iconic pixie cut era.

At the 1997 Academy Awards, Ryder showed how glamorous a short hairstyle can be with her sleek, jet-black pixie. Neatly parted and coiffed, the look was giving Old Hollywood vibes — an aesthetic only heightened by her shadowy eyes, crystal earrings, and timeless red lip. But Ryder is no one-trick pony — barely a year later, she showed off an entirely different twist on the pixie while attending the 1998 Cannes Film Festival in France. The choppy, caramel-tinted cut was charmingly boyish, giving Ryder a cheeky yet approachable air.

After years of edgier haircuts, Winona Ryder stunned at the 2001 Academy Awards by arriving with a surprise of blazing strawberry-blond tresses. The wavy, romantic look was a departure from her previous styles, with vibes a lot closer to Rose from "Titanic" than Lydia Deetz from "Beetlejuice." It was an incredible and timely refresh. As Ryder's own stylist Philip Carreon told InStyle, "She has always been cast as the young woman with the pixie, and at this point in her career, she wanted a more adult look." Of course, this adult look didn't mean that Ryder was above having a little fun. During this period, the actor starred across from Adam Sandler in the comedy "Mr. Deeds" and even made a cameo in "Zoolander."

Ryder continued to show off her lighter hair color through 2004, including an elegant turn at that year's American Museum of the Moving Image Benefit, where she appeared with her auburn hair pulled back in a sleek chignon. And as much as we adore the star's usual high-contrast look of dark hair against a pale complexion, this styling proved that a softer, warmer hair color also does amazing things for her skin tone.

After her foray into romanticism, Winona Ryder returned to her comfort zone: short, dark hairstyles. For the LA premiere of her sci-fi thriller "A Scanner Darkly" in 2006, Ryder wore a curly bob that brought her signature look firmly into the second half of the noughties. Paired with a thin choker necklace and the even thinner straps of her camisole dress, it was flirty '00s chic.

Ryder also attended the 2009 Hollywood premiere of "Star Trek" — in which she portrayed Spock's mother Amanda Grayson — with an adorably truncated hairstyle. The slicked-back 'do was once again hitting that pixie-bob midpoint that characterized her early '90s bixie, but Ryder modernized the look with a bit of volume and then dressed it up with the addition of a sparkling black headband. The overall result was just space-age enough to suit the film without going overboard, proving that red-carpet fashion can be referential without being costumey.

By 2010, Winona Ryder seemed ready for another change in both her style and career. Adopting a more natural haircut, Ryder breezed through public appearances with free-flowing brunette curls. At an LA press conference for her film "Homefront" in 2013, Ryder wore her long hair with a casual, hand-swept side part that played well with the effortless cool of her black blazer ensemble.

Professionally, it began to look like Ryder had transitioned from a headliner to a solid supporting actor, but her 2016 casting as Joyce Byers in the Netflix phenomenon "Stranger Things" quickly thrust Ryder back into the spotlight and the public consciousness. Still, she held onto her more laid-back styling, attending events with long cuts and classy updos. For instance, Ryder once again let her hair down at a "Stranger Things" Season 3 press conference in 2019, with soft, gently curled waves that flattered her natural makeup look for the event.

But beneath this polished exterior, Ryder was still the pop culture anti-hero we know and love. After all, who could forget the juxtaposition of Ryder's gorgeous curled updo and wacky mannerisms at the 2017 SAG Awards? The actor reacted to "Stranger Things" co-star David Harbour's speech with a series of facial expressions that launched a thousand memes.

Catching up with the Winona Ryder of today, it seems like this accomplished actor is still as quirky as ever — and has once again altered her hairstyle to reflect her lovable individuality. In 2022, Ryder appeared at the New York premiere of "Stranger Things" Season 4 rocking a trendy wolf haircut, and rocking it better than most. Since then, it's become a staple for the star, who has been spotted in a similar cut through 2023 and 2024.

While the wolf cut's 2022 heyday may have died down in overall popularity, we have to admit that it suits Ryder's energy to a T. As for everyone else, the wolf cut isn't the only option out there for the shag-curious. There are dozens of shag haircuts to inspire your next salon visit, whether you're looking for something notably vintage, curl-friendly, or free-spirited and beachy to channel your inner Winona.