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30 Best Celebrity Style Transformations

Angelina Jolie

Angelina Jolie has had a bit of a weird past. There were rumors about her love affair with her brother and the odd relationship with Billy-Bob Thornton. Her fashion sense reflected that time in her life. She almost always dressed in grunge, but all that changed when she got older. Now, she’s the epitome of classy.

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Drew Barrymore

Drew Barrymore had a rough childhood. She was an alcoholic at 11 and a drug addict by 12. Over the years, she cleaned up her act and became one of the best actresses of her age. When she was younger, she wore what any teenager would wear – jeans and a t-shirt. As she grew, she went grungy, but it didn't last long. She eventually got into fashion and made her own makeup line called FLOWER Beauty. To match that, her style has improved. 

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Kelly Osbourne

Whether it was for attention or just a statement, Ozzy’s daughter, Kelly Osbourne, had a unique fashion sense when she was younger. While she still has a flair for the odd (like purple hair), she completely changed the way she looked. She lost weight and started to wear outfits that were quite fashionable. She still loves darker colors, but there's no more grunge.

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Harry Styles

Harry Styles popped up with the UK band One Direction. It took England and the United States by storm, but he couldn’t wait to bust out of his shell. When he did, he ditched the drab colors for something more. Today, this little up-and-coming performer is often seen wearing flashy suits or jackets with elaborate designs. It’s anything but drab and dull.

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Beyonce

Beyonce was a member of Destiny Child, and her style often reflected what the other members wore – they had to match! Because she grew to popularity during the ‘90s, she wore what was popular. That was usually jeans with designs and bandana or halter tops. However, she went solo, and everything about her changed. She became much classier, and this Queen of Music became a fashion icon.

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Lady Gaga

Lady Gaga showed up on the scene looking like something that would rival Britney Spears. She was designed to be the new “Pop Princess,” but it didn’t last. Gaga started to dress weird (to say the least), but she wanted to use her brand as a way to speak up for issues that mattered to her. She wore a meat dress and came out with “Born This Way” for social causes. While her outfits still vary quite a bit, it’ll be tough to catch her in a Brittney-esque outfit again.

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Julia Roberts

Anyone that grew up in the ‘80s can tell you that you had to have a power suit with shoulder pads to be considered an adult. This was Julia Robert’s style in the ‘90s. In fact, she wore a power suit to the golden globes in 1990. We’re happy to say that she dresses much different nowadays. She can be classy, like when she’s at an award show, or casual when she’s just sitting at the beach.

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Brad Pitt

Gone are the Fight Club days – well, sort of. While Brad Pitt doesn’t look as young anymore, he still looks pretty dang good. In the ’90s, he looked more like a surfer boy or a bad boy, but with time comes change. Brad is now a father and dresses like one when he’s out and about. He kept the long hair, but we’re happy to see that he styles it somewhat.

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Pink

Her name may be Pink, but she doesn’t have pink hair anymore. Now, the mother of two has opted for blonde hair, but you may also see her with very pastel pink hair. She followed suit with a lot of stars during the time. Some of her outfits were downright strange, like a floor-length green and blue jacket. Pink still dresses a little grungy, but she now matches.

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Nicki Minaj

Nicki Minaj came into the game singing pop, but she was always active in the rap scene. As she became more popular, she was able to do what she wanted, and she went from Starships to Chun-Li. Her style also changed. Less purple, less color, and more natural. Nicki now rocks her natural hair color and wears clothing that’s much more flattering.

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Victoria Beckham

Victoria may have been Posh Spice in the ‘90s, but now she’s a businesswoman, fashion designer, and model.  Back then, wearing platform shoes and revealing clothing was just the way things were. Now that she’s married and a designer, she has changed her looks. Now, she’s always classy, and she’s regained the name “Posh.” If you use anyone as a style icon, it should be Victoria Beckham.

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Taylor Swift

Once upon a time, Taylor Swift was going to be a country music star. One thing led to another, and she ditched her boots for booties and heels. She quickly became a fashionista as she moved into pop. It’s hard to find her walking around without wearing something totally stylish.

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Miley Cyrus

Even though Miley Cyrus hasn’t been around for very long, she’s been through a ton of styles. She went from a Disney star to a wild child. Then, she got a little more conservative when she stopped humping foam fingers. She loves the casual style of jeans and a t-shirt, but you might see her dressed up every now and then.

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Anne Hathaway

When Anne Hathaway was trying to find her way in Hollywood, she wasn’t really sure how to dress. She often went for colorful pieces with intense designs. Now that she’s older, she chooses more neutral colored outfits. Hathaway also manages to always look incredibly elegant no matter what she’s doing. We’re not sure how she does it.

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Gwen Stefani

Gwen Stefani was the lead singer of No Doubt, a band that rebelled against modern music. Her style was erratic. It was like every day was an outdoor festival for her. Skip ahead a decade (or more), and Stefani has changed completely. Her outfits are still incredibly stylish, but she doesn’t show off her body as much as she did before.

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Justin Timberlake

Justin Timberlake became an icon in the mid-'90s, and since then, he's made a name for himself as an outstanding solo artist following the break up from the boy band NSYNC. As he made a name for himself, he ditched the early-2000s fashion disasters (like that all denim outfit he rocked with Britney in 2001) for a more sophisticated and grown-up look.

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Leonardo DiCaprio

In the late '80s and early '90s, DiCaprio was known for wearing shallow-knit skull caps and baggy bowling shirts, but as he got older, it was easy to see his style improved. DiCaprio began to wear perfectly tailored suits in classic monochromatic colors on the red carpet and casual cargo shorts for his days off. No matter the occasion, DiCaprio knows how to impress.

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Cher

Cher has always been a style icon in her own league with very few competitors that could even hold a candle to her iconic looks. Cher has never been one for subtlety, opting instead for bright colors, bold statement pieces, and dramatic accessories (e.g., those headpieces). Now, Cher has mostly traded in her wild headpieces and outfits for a more toned-down style on the red carpet (though, she does still have the wild getups for her tours).

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Nicole Kidman

In the late '90s and early 2000s, Kidman experimented with shimmering colors and bold, bright colors. Though in more recent years, Kidman's gravitates toward neutral designs with a bit of sparkle to glam (rather than overwhelm). Even after all these years, Kidman still manages to wow everyone on the red carpet!

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Robert Downey, Jr.

In his early years back in the late '80s, Downey never feared bold statement pieces and out-of-the-box (putting it mildly) looks. For example, the shorts and suit jacket he wore for the premiere of Chances Are back in 1989. After battling addiction and landing the role in Iron Man, his style was significantly changed. Downey went from too-big suits to perfectly tailored and flattering tuxes. Though, he still likes to pull off a bold look occasionally.

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Caitlyn Jenner

Probably the most drastic change on this list, Caitlyn Jenner (formerly Bruce Jenner) reintroduced herself to the public on the cover of Vanity Fair's June 2015 edition after breaking off her marriage with Kris Jenner. Jenner has always been a fashion icon after debuting as an Olympic Gold Athlete at the 1976 Summer Olympics in Montreal, with bright jackets and classic suits. Now, Jenner sports gorgeous, flowing gowns for the red carpet and cute, casual skirts for everyday life.

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Demi Moore

Demi Moore emerged onto the scene in the early '80s, sporting a set of blunt and choppy bangs that quickly turned into a more teased and puffed out style to match her eclectic personality. Since then, her wardrobe has changed drastically and, after her marriage to Ashton Kutcher, her style seemed to take on a younger, more designer-focused look.

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Jennifer Lopez

Jennifer Lopez has been known for bold and iconic looks (that Versace gown from the Grammy Awards in 2000 attests to that), and her style has switched several times (from sheer to sequins, to hip-hop, and everything in between). As the years have gone, Lopez's style has evolved into something refined and classic, while still maintaining that bold and iconic style that has landed her on several best-dressed lists.

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Madonna

With a career that has spanned the better part of four decades, it's expected that Madonna would have influenced the fashion world considerably. From her iconic 1984 'Like a Virgin' wedding dress and the cone bra during her Blonde Ambition Tour in 1990, Madonna's style has seen many iterations, but it currently rests in a niche between dark, edgy, and trendy. FYI, we love it.

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Scarlett Johansson

Starting as a childhood star, Johansson's style quickly morphed from innocent to provocative as she grew in the Hollywood industry. At least until the early 2000s hit, which is when all good fashion went down the drain. Thankfully, Johansson managed to mostly shield herself from the nightmarish outfits of the early 2000s, and since then, her style has come to reflect a classic and sophisticated style that we can't get enough of.

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Charlize Theron

Early Charlize Theron's style had a staple of stripes and pantsuits, but throughout the years we can see her style evolve into something dark and sophisticated with long, form-fitting dresses and the occasional dark pantsuit. Monochromatic colors like black, white, and grey with occasional pops of color has always been a Theron staple. Though now, she's slowly making more edgy fashion choices (though still in those dark colors that she does work so well) with lace tights under dresses and lots of fringe.

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Winona Ryder

The star of the movies Heathers and Beetlejuice, Ryder has tried basically every look in the book, jumping from grunge to girly and everything in between. Her role in the cult classic movies have cemented her as a staple in pop culture, but her style is still something that no one can really get over. She's grown from the '90s grunge of mom jeans and a black leather jacket to a more refined, red-carpet-esque glamor look.

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Jennifer Aniston

Aniston has been a style icon since the early '90s, but her style really hit a high when she joined Friends in 1994 and created the classic "Rachel" haircut that still reigns in popularity today. Classic hairstyle aside, Aniston is known for her bold style choices (like wearing a tube top and maxi-skirt to the 5th Annual Screen Actors Guild Awards in 1999). Some constants in her ever-evolving style are those gorgeous pantsuits and Little Black Dresses that continue to grace her wardrobe and wow us all.

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Courtney Love

An early 90's grunge style icon, Love was known for her usually-all-black daring, and one-of-a-kind looks paired with dark makeup and styled-messy hair. After the death of her husband Kurt Cobain, Love left the punk style behind and opted instead for a more classic Hollywood glam look. Though she still likes to throwback to her punk rock roots occasionally.

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Johnny Depp

Johnny Depp easily has one of the more whimsical and eclectic styles on this list. After his initial appearance in the '80s with t-shirts, leather jackets, and fun hats, Depp upped his game very quickly to include fashionable suits in wild colors, vests, and his traditional leather jacket. His biggest asset in his out-there outfits are his accessories (hats, scarves, and sunglasses, specifically). Depp always knows how to wow us with his daring looks.

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