Side By Side Pics Of Winona Ryder Show Her Head-Turning Transformation

These days, Winona Ryder is best known as the harried, determined mother Joyce from "Stranger Things." The beloved actress has carved out a second career era as a mom — in the "Beetlejuice Beetlejuice" sequel as well — but once upon a time, she used to be among Hollywood's favorite leading ladies. She was a major It Girl of the '80s and '90s. First, she was known for playing quirky, edgy heroines like Veronica from "Heathers." Later, she earned a reputation for portraying romantic leads like Jo from "Little Women" or Finn from "How to Make An American Quilt," blending undeniable beauty with natural, boyish charm.

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Ryder's evolution as an icon is part of what makes her an enduring Hollywood figure, even 39 years after she first began acting. In an interview, she acknowledged that her place in Hollywood has changed. "You're the girlfriend, then you're the mother. But I don't see it as a bad thing, It can be just as interesting, if not more so, than the leading-lady, ingénue phase," she told The Edit (via ABC).

Ryder looks undeniably different these days, but the change seems to be the natural effects of aging, rather than any significant surgical alteration. While many of her contemporaries are getting fillers and Botox, Ryder appears to have opted out of any cosmetic enhancements. "I love the way she's letting her face continue to mature," wrote one Reddit commenter. "She's a forever beauty."

Cosmetic enhancement might be the new normal for aging actresses. Still, Ryder is one of a few celebs who have been vocal about avoiding plastic surgery. She's avoided anti-aging procedures her face, even when the industry has pushed her to get Botox, in part because it gets in the way of her acting process. "They'll say, 'Just relax your forehead. Relax,'" she told Elle. "I'm trying to be a great actor, and they're saying that over and over." For Ryder, it seems, the priority has been maintaining an expressive freedom of movement in her face.

For Ryder, getting up in her years isn't a terrible thing, and she's one of many celebs that are confronting aging with confidence. "Getting older, there are things that obviously suck, like bone density," she said in conversation with Tavi Gevinson for Interview Magazine in 2025. "But there's so much great stuff with it." Of course, she might be older, but in fashion at least, Winona Ryder is still the reigning queen of grunge style. She favors edgy red carpet looks, and almost always in the color black.