Top 10 Celebs With the Biggest Style Transformation

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Top 10 Celebs With the Biggest Style Transformation

VOICE OVER: Kirsten Ria Squibb WRITTEN BY: Robin Schwartzkopf
Like a butterfly from a cocoon, these celebs have the biggest style transformations. Our countdown includes Angelina Jolie, Zayn Malik, Zendaya, and more!
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Top 10 Celebs With the Biggest Style Transformation


Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Celebs With the Biggest Style Transformation.

For this list, we’ll be looking at stars who have shifted their wardrobes dramatically over the course of their careers.

Which star do you remember rocking a newsboy cap or velour tracksuit who would be unrecognizable today? Let us know in the comments below.

#10: Angelina Jolie


This actress, director, and humanitarian has been a standout on red carpets since the start of her career in Hollywood. However, her style has changed dramatically over the years, going from rocking monochromatic, alternative looks, to more elegant and high fashion ensembles. In the early 2000s, Jolie was known for her dyed black hair and penchant for wearing leather. By the middle of the decade, her fashion took a more elevated turn, with her opting for Versace on many red carpet occasions. In her role as Special Envoy to the United Nations High Commissioner for Refugees, Jolie has opted for professional and sleek attire while still preserving a bit of her early edge with a black-heavy color scheme.

#9: Taylor Swift


This pop superstar shakes off old fashion trends and keeps moving forward. In her early years of fame, Taylor Swift was a country princess with a wardrobe to match, often rocking cowboy boots and sundresses, rarely seen without her acoustic guitar. As she produced more albums and gravitated towards pop music, Taylor switched up her look accordingly. Her performance attire, red carpet ensembles, and streetwear tend to reflect her current album cycle. In the early 2010s, the musician almost always chose a red lip. In 2014, she cropped her hair and most of her tops. Her cottagecore, Americana aesthetic began in 2020 with the release of her more alternative record, “folklore.” Taylor Swift keeps transforming, and will likely do so until she stops releasing music.

#8: Zayn Malik


Before he was on the cover of Vogue, he was a boy in a band. Like his other One Direction members, Zayn Malik’s style shifted considerably as he grew up with the group. When the UK-based boy band was still on “The X Factor,” Zayn opted for casual teen attire. Bomber jackets, sneakers, and clean-cut suits for the red carpet made for a safe style. He began experimenting with different hairstyles and more tattoos in music videos and public appearances, but really made his mark when he departed the group in 2015. He debuted a buzzed haircut and would soon appear on Instagram and in magazines with more alternative styling. Zayn also upped his fashion game in his longtime romantic relationship with supermodel Gigi Hadid.

#7: Blake Lively


This actress has always been recognizable due to her long, wavy blond hair. However, her wardrobe has changed quite a bit since the days of the “Sisterhood of the Traveling Pants.” In 2005, Lively’s approach to red carpets was more casual. After being cast in the hit teen soap series “Gossip Girl,” she updated her wardrobe with more high-fashion and sleek pieces. Now known to the world as her character Serena van der Woodsen, Lively opted for monochromatic looks in bright colors for her red carpet appearances. In the late 2010s, her iconic run of looks at the Met Gala further elevated her style status.

#6: Victoria Beckham


As Posh Spice, Victoria Beckham was known to rock a sleek look onstage or in a music video. Flash forward a few decades and she is a fashion mogul in her own right. As part of the British girl group, Beckham experimented with her look by coloring her hair and wearing a lot of bodycon dresses that don’t really match with her newer, more elegant aesthetic. Her chic and high-fashion wardrobe has made her a style icon. She has since become a fashion designer in her own right with her eponymous label, which launched in 2008.

#5: Miley Cyrus


This actress and singer went from child star to rebel rocker, with a few fashion eras in between. On the show “Hannah Montana,” Miley was dressed in layers of colorful clothing. After the show ended in 2011, an independent Miley pivoted to a more mature look. In the following years, the musician’s style changed with her music, as she went from vibrant and daring party looks around the release of her album “Bangerz” to cowboy boots and flowing, beachy waves in her hair for her country-pop album “Younger Now.” In 2020, she turned to her glam rock roots with flair and a fresh mullet haircut. She’s a far cry from her “Party in the U.S.A.” days, but her fashion is on another level.

#4: Meghan Markle


There aren’t as many rules when you’re an actress on “Suits.” When Meghan Markle married Prince Harry and became Meghan, Duchess of Sussex, her style became a topic of international interest. In her earlier career as an American actress, Markle still dressed with a sharp eye and favored cocktail dresses for red carpet events. After joining the royal family, Markle had to avoid dresses that were above the knee and many different, less professional styles. Her style got sleeker and elevated in terms of designers. After she and Prince Harry stepped down as members of the royal family, her attire has evolved into a mixture of elegant fashion and calculated stylistic experiments.

#3: Kim Kardashian


Kim K’s early reality days are a far cry from her fashion after “Keeping Up with the Kardashians” made her a household name. Kim’s fashion in the early 2000s was on-trend for her burgeoning celebrity life in the valley. She wore plenty of wide belts, big sunglasses, and tracksuits. Her style shifted dramatically in 2012 when she began dating Kanye West. In her marriage to the rapper and fashion designer, Kim became known as an icon for athleisure and luxury looks. She swapped her vibrant colors for a more neutral palette and daring silhouettes. She also started her own line of undergarments and loungewear which she often rocks in her streetwear and on social media.

#2: Zendaya


This mononymous actress has always shown her experimental side on the red carpet, even as a child star. After rocking kid-friendly, layered, and busy looks while on the Disney show “Shake It Up,” Zendaya maintained her colorful outlook and started switching up her silhouettes. Her sleek, elevated, and creative looks started to turn heads. She made a name for herself at the Met Gala in 2017, 2018, and 2019 as well, cementing her status as a major fashion player. Zendaya was announced as the new face of Valentino in 2020 and continues to push sartorial boundaries in her streetwear and luxury looks.

#1: Harry Styles


Like his former bandmate Zayn, Harry Styles transformed his wardrobe after One Direction. Styles began developing his sense of style upon auditioning for “The X Factor” in 2010, gravitating towards casual looks during the band’s early years. Before the boys went on hiatus in 2016, Harry started to show signs of his fondness for Chelsea boots and button-down shirts. When he released his first solo album, his tour became a showcase not only for his musical talents, but for an array of colorful and expressive tailored suits. His creativity only expanded with his sophomore record, which saw him experimenting more with mixing patterns and textures and flaunting gender norms while performing and in public appearances.
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