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How the Looks of 19 Style Icons Have Changed Over the Years

Celebrities don’t usually start their careers with fashion stylists and access to designer clothes. Like us, they have to work with what they have. It takes years to develop a signature sense of style. And even then, they often surprise us with something new.

Bright Side would love to take you on a walk down memory lane with these style icons who have changed their look more than once.

1. Ariana Grande

Ariana Grande started working on the launch of her music career in 2010. And over the years, we’ve seen her cute style develop to become more feminine and elegant as she became a pop icon. But it seems that, despite her look’s evolution, there is one feature that she likes to stick to. And that is her thick and luscious ponytail which she often wears on glamorous occasions like the 62nd Grammy Awards in 2020.

2. Christina Aguilera

In the early 2000s, Christina Aguilera felt free and wanted to push the boundaries of fashion. She showed her “dirty” side and wanted to completely get rid of the image of a good girl. Since 2018, she has opted for more minimal makeup, often with a nude and natural look.

3. Johnny Depp

Johnny Depp has always dressed creatively. However, he is not always laid back in his signature scarfs and fedoras. He has replaced this rugged look with sleek tuxedos and suits on many occasions.

One such occasion was the Monte-Carlo gala for planetary health where Johnny sported a classic tux with a twist on the traditional bow-tie

4. Anne Hathaway

Anne Hathaway entered the movie scene in 2001 with her breakthrough role in the Princess Diaries. She’s since ditched the dress and jeans combo but still graces the red-carpet like a princess 20 years after the release of the movie.

5. Emma Watson

Emma Watson has refined her style over the years since her early Harry Potter days. She even recently joined the board of directors for a parent company that owns luxury brands like Gucci and Balenciaga. Her fashion diversity is most likely what makes her a style icon as she is known to pull off both tailored suits and feminine gowns.

6. Taylor Swift

Taylor Swift started her career doting cowboy boots and sparkly dresses. As she became more successful, her style matured. She has since forgone the boots and replaced them with her signature red lipstick.

7. Jared Leto

Just like his career, Jared’s style has gone in many directions. During the ’90s his rock band 30 Seconds to Mars was formed. Of course, Jared had a rock star style to match. More recently, Jared has an eclectic style and embraces the ’70s with his long flowing hair and graphic suits.

8. Miley Cyrus

Miley Cyrus has changed a lot from her Disney days. She has taken many style risks to arrive at where she is today. She hasn’t completely left her grunge-wrecking ball phase behind and still has an edgy sense of style.

9. Scarlett Johansson

There is a 13 year difference between these 2 photos of Scarlett and the style changes are crystal clear. From a quirky pink dress to a sultry red dress, Scarlett has always let the clothes speak for themselves.

10. Sandra Bullock

Sandra Bullock has often been dubbed America’s ’90s sweetheart. She has now gone on to win many awards. Her bold color choices and angular haircut are just as successful as she is.

11. Nicole Richie

Nicole Richie has had a whirlwind style transformation. She started as a Y2K socialite, alongside longtime friend Paris Hilton. Her early style definitely followed the trends of the time. However, over the years she found her own look.

She has now switched out rhinestones and thin scarfs for preppy looks or boho dresses and even embraces her natural curls.

12. Kate Middleton

Kate’s style change was relatively rapid, as is expected from someone who went from everyday college girl to Duchess, seemingly overnight. She has left her miniskirts behind and now wears classic modest styles that are fit for a queen.

13. Jennifer Lopez

Jennifer Lopez is such a style icon her 2000s Grammy Awards dress is said to have kick-started Google images. In her early days on the red carpet, Jennifer Lopez took inspiration from street style. She then shifted her focus to sleeker and more clean-cut dresses, and is no stranger to the best-dressed list.

14. Reese Witherspoon

Reese Witherspoon has a unique fashion sense that cannot be boxed into one category. She often incorporates tailored fits and bold colors into her style. What’s more, her outfits are known to be inspired by whatever project she is working on at the time. For example, she mostly wore pink on the red carpet while promoting her film Legally Blonde.

15. Justin Timberlake

From teen pop star in NSYNC to black tie suits, Justin has changed quite a bit.

16. Drew Barrymore

Barrymore is no stranger to exploring different aesthetics. She was inspired by ’90s grunge during her teenage years but has also dressed in exactly the opposite manner in flowing gowns.

17. Lady Gaga

Lady Gaga has become a household name not only because of her successful music career but also because of her outlandish and daring fashion statements. Although she is still no stranger to the avant-garde, her style has refined and simplified itself over the years.

18. Meghan Markle

Although Meghan has shifted her silhouettes to conform to the more conservative style of royal life. She is still a rule-breaker and has not forgone her personal fashion sense. She still favors simplicity and monochrome fabrics.

19. P!nk

P!nk made her debut in 2000 rocking a pink pixie haircut which then became her signature style for years. But she once experimented with a different hairdo for the Billboard Music Awards in 2001. The blond and pink dreads make for another unforgettable look in the singer’s style evolution. Nowadays, P!nk still rocks her short hair in platinum color, as seen during the premiere of her video documentary in 2021.

Which celebrities do you think have been through a complete style transformation? Are there any celebrities whose old look you prefer to their new one?

Please note: This article was updated in February 2022 to correct source material and factual inaccuracies.
Bright Side/People/How the Looks of 19 Style Icons Have Changed Over the Years
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