See 10 Celebrities Who Underwent Major Style Transformations

Joyann JeffreySun, June 21, 2026 at 11:30 AM UTC

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Miley Cyrus on Aug. 20, 2006, in Universal City, Calif. ; Harry Styles on Jan. 22, 2012, in London; Zendaya on Aug. 28, 2010, in Beverly Hills, Calif.Credit: SGranitz/WireImage; Jo Hale/Getty; ANDREAS BRANCH/Patrick McMullan via Getty

Celebrities' images are constantly evolving in Hollywood.

Whether it's a subtle shift toward a more sophisticated look or a complete reinvention that leaves fans doing a double take, celebrities often use fashion as a way to reflect new chapters in their lives and careers.

Former child stars like Zendaya and Miley Cyrus have grown up in the spotlight, and naturally, have changed their looks over the years.

Cyrus rocked trendy graphic tees and capri leggings in her years playing Hannah Montana in the hit Disney Channel series. While her fellow Disney Channel alum Zendaya wore plenty of vests, neon tights and high-top sneakers during her years portraying Rocky Blue on Shake It Up.

Here are 11 stars who have undergone major style transformations over the years.

01 of 10

Kylie Jenner

Kylie Jenner in 2015 and 2026Credit: Jamie McCarthy/Getty; Karwai Tang/WireImage

Kylie Jenner's King Kylie era was monumental. In the mid 2010s, the reality TV star dyed her hair in colorful hues and took bold chances with her makeup.

"I think that I'm kind of a chameleon with my style; I love to play. I've been like that since I was 16," she told Harper's Bazaar in May 2025 about that time in her life. "I changed my hair color like once a week and cut my hair off and then put a wig on or put extensions in; and I've always switched up my style."

However, Jenner has since changed her look, often wearing her natural hair color. She also spoke to Elle in October 2024 about growing out of her former style and deciding to refrain from certain trends.

"I probably would never wear lash extensions and thick eyebrows," she said. "There are just certain trends that I've grown out of."

02 of 10

Kourtney Kardashian

Kourtney Kardashian in 2015 and 2022Credit: Andreas Branch/Variety/Penske Media via Getty; Jamie McCarthy/Getty

Kourtney Kardashian's style has changed a lot over the years. The Poosh founder has been leaning more into the rockstar aesthetic ever since she began dating her now-husband, Travis Barker.

Kardashian — who used to wear a lot of feminine looks — began opting for more leather outfits, band T-shirts and black clothes. She has also shared a photo on Instagram wearing a white T-shirt, long black shorts, crew socks and sneakers, captioned, "Husband's clothes forever."

03 of 10

Taylor Momsen

Taylor Momsen in 2006 and 2026Credit: Jesse Grant/WireImage; Brianna Bryson/WireImage

Taylor Momsen is another celebrity who is a fan of the edgy grunge look. In a February 2021 interview with PEOPLE, the Gossip Girl actress recalled the moment her style started to take form and said it happened once she started her band, The Pretty Reckless, as a teenager.

"The phase was the stripper heels and the outrageous outfits," she said. "But at the time, that didn't feel like a phase. That was very much who I was and how I was comfortable dressing. Like anyone, I grew and I matured."

04 of 10

Susan Boyle

Susan Boyle in 2010 and 2025Credit: Dave J Hogan/Getty; Mike Marsland/WireImage

In 2009, the world was introduced to Susan Boyle when she sang a rendition of "I Dream a Dream" from the musical Les Misérables on Britain's Got Talent.

For her audition, she sported a short curly hairstyle, which she later straightened into a brown bob. After keeping this style for many years, Boyle changed up her look in May 2026 as she prepared to release some new music.

She shared a photo on Instagramshowing off her straight blonde hair and wearing a brown velour tracksuit and a fur coat.

"A new era starts tomorrow," she captioned the post.

05 of 10

Mary-Kate and Ashley Olsen

Mary-Kate and Ashley Olsen in 2005 and 2026Credit: Jamie McCarthy/WireImage; BrosNYC / BACKGRID

Mary-Kate and Ashley Olsen's early red carpet style featured more colorful looks and fun and flirty dresses. But as the twins got older, they started to dress more neutral and donned black more than any other color.

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"We were raised to be discreet people," Mary-Kate toldi-D in June 2021 about how her and Ashley's fashion line The Row relates to them personally.

Ashley added, "I think that potentially that's just our aesthetic, our design preference."

"But that doesn't mean that we don't also appreciate something truly ornate or maximal," she continued. "Sometimes a collection even starts quite like that, and then gets pared down. It doesn't always start from that simplistic place."

06 of 10

Miley Cyrus

Miley Cyrus in 2007 and 2026Credit: Jeff Kravitz/FilmMagic; Monica Schipper/WireImage

Cyrus has had quite the style evolution.

The Hannah Montana alum used to wear colorful, sequin-filled outfits during her childhood. However, everything changed around the release of her third studio album, Can't Be Tamed.

After that, Cyrus settled into a rocker chic aesthetic and has continued wearing daring looks over the years.

07 of 10

Kristen Stewart

Kristen Stewart on Sept. 7, 2008, in Los Angeles; Kristen Stewart on Jan. 9, 2026, in Santa Monica, Calif.Credit: Jeffrey Mayer/WireImage; Christopher Polk/WWD via Getty

Kristen Stewart has been walking red carpets ever since she was a little girl.

When the actress got her big break on Twilight, Stewart was wearing sweet cocktail dresses to Hollywood events. As she started getting older, Stewart began experimenting more with her style, including a brief stint with hot pink hair in the summer of 2025.

She now embraces an edgier look that includes a mullet hairdo, crop tops and bodysuits and dark colors.

08 of 10

Zendaya

Zendaya in 2010 and 2026Credit: ANDREAS BRANCH/Patrick McMullan via Getty; TheStewartofNY/WireImage

Zendaya started out on Disney channel, often wearing very colorful outfits much like her Shake It Up character. She soon partnered with stylist Law Roach, who helped her become one of the biggest style icons to date as her career progressed.

In addition to her unique method dressing based on projects she is in, Zendaya now often wears sleek, sophisticated looks. She has also traded in her wavy, long brown locks for a chic bob hairstyle.

09 of 10

Harry Styles

Harry Styles in 2012 and 2023Credit: Jo Hale/Getty; Dave J Hogan/Getty

Harry Styles has come far since his time on The X Factor, when he and his One Direction bandmates used to sport plain white tees and skinny jeans.

Now, Styles often opts for more bold, gender fluid outfits, including colorful suits, feathered boas and sparkly jumpsuits.

10 of 10

Ariana Grande

Ariana Grande in 2010 and 2026Credit: Angela Weiss/Getty; Maya Dehlin Spach/2026GG/Penske Media via Getty

In a January 2014 Facebook post, Ariana Grande said she had to bleach and dye her hair red "every other week for the first 4 years" of playing Cat Valentine on Victorious.

"As one would assume, that completely destroyed my hair," she said, explaining how it led to her signature ponytail era.

Grande wrote that she wore a ponytail at the time because her hair was "so broken" that it looked "absurd" when she let it down.

Fast forward to 2026, the singer has worn her natural curls and has returned to brunette hair after being blonde for three years for her role as Glinda in Wicked.

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