Winona Ryder's Signature Short Hair Styles From The '90s Deserve To Make A Comeback

Looking for some unique inspiration for your next haircut? Winona Ryder had an array of iconic short hair styles in the '90s that were beautiful, edgy, cool, and timeless — and each one is more than worthy of a comeback in the modern era. It's true that Ryder has had a stunning transformation over her decades-long career, but there is something about her '90s-era beauty that really stands out for the "Dracula" star.

In an August 2025 interview with Elle UK, the "Edward Scissorhands" star looked back on this time in her life. "All during the '90s I cut my own hair," Ryder shockingly revealed, demonstrating how she would put her head down and cut it in a choppy, unplanned way with scissors. "And I did that for most of any of my short hair," she added. "You'd start with the bangs, and then you'd, unfortunately, have to take it all off."

Because of her completely random and unplanned way to style her hair, Ryder admitted in the interview that she was "incredibly surprised and flattered" when this short hairstyle became popular, with girls bringing her picture into their hair salons and asking for recreations. Little did they know they could have just done it at home by themselves! Now, we are obsessed with these looks once again, which is no surprise given that short hair styles dominated the red carpet in 2026.

Winona Ryder's short bob was slicked back and gelled away from her face in this photo from 1990. Unlike a flat, combed-back look, Ryder's hair had volume when it was pulled back making it stand out in a fresh way. We love how this style kept her face open so you could see all her beautiful features. Plus, the bob-length of her hair was super cute as well, making the overall style look perfect. 

Winona Ryder embraced old Hollywood glam at the 68^th Academy Awards in 1996, when she showed up in a gorgeous white, sequined gown with her short hair in finger waves. For those unfamiliar, finger waves were a popular 1920s style, with short hair sculpted around a finger in a chic S-shape. Because Ryder's hair was cut in a pixie cut, with long bangs on one side, she was able to showcase this style effortlessly. And you can totally recreate this look at home!

Micro-bangs, or baby bangs, looked edgy and cool on Winona Ryder. She rocked this style at the "Girl Interrupted" Los Angeles premiere in 1999, with her hair in a messy pixie cut and tiny, extra-short bangs lying unevenly across her forehead. This hair, paired with the dark-mauve lipstick and dark mascara, made her look mysterious. Fuller bangs have been trending in the 2020s, so it would be nice to see a return to this shorter style.

While attending the "Edward Scissorhands" premiere alongside Johnny Depp in 1990, Winona Ryder's hair was dyed jet black and styled in a straight bob past her chin. Her hair was parted in the middle and curled toward her face at the ends. This sleek style framed her face and drew attention to her features without bangs. It was definitely longer than most of her '90s looks, and it still looked great on her.

In 1994, Winona Ryder was growing out her pixie cut and wore her hair in a fun, mullet-like style. In a picture promoting her film "Reality Bites," Ryder looked otherworldly with her glowy skin and big, open eyes as she stared at the camera. Her hair was the main attraction, as it was cut short in front of her ears and parted to one side, then hung long to her shoulders in the back.

Winona Ryder's uneven bangs stole the show at The New York Film Festival in 1998. In a picture from the event, her pixie cut covered her ears in the front and stood up at all ends on top, almost like she just rolled out of bed. (Although, we bet it took meticulous styling to achieve this seemingly effortless look!) Her bangs were cut unevenly across her forehead and styled in messy pieces, which looked truly iconic.

When Winona Ryder showed off her Golden Globe for Best Supporting Actress for "The Age of Innocence" at the 1994 award show, she looked glamorous with the chicest short hairstyle. At this time, she had a classic pixie, cut short on the back and front. She gelled her hair in place, with her bangs in a side part, which was a much different vibe from the messier style she would wear a few years later. The close-cropped hair looked timelessly beautiful, especially paired with her black dress, pearl necklace, and matching pearl bracelet.

Blonds have more fun — or so it seems. Just ask Winona Ryder, who was all smiles in a photo with her highlighted hair at the Nantucket Film Festival in 1996. Her typically dark hair was much lighter with its strawberry blond color, which looked fabulous with her short hair. She had pieces falling over her ear and on her forehead — the perfect mix between bedhead and every strand gelled in place. With her bright, genuine smile, this whole look is one of our favorites!