The Most Dramatic Celeb Makeup Transformations

There are some stars you can count on for consistency with their style, like Julia Roberts, Zooey Deschanel, Lucy Liu, or Gabrielle Union. They may change things up slightly, but you can almost always count on them for their signature looks (a wide smile, dark bangs and bright eyes, stunning dark hair and golden skin, and preternaturally glowing skin). 

Others, however, have made such drastic changes to their makeup styles throughout their careers that they look like completely different people. I talked to top makeup experts about these celebs who have all transformed their makeup in huge ways over time...though a few may have had help from doctors, too.

At the 1993 American Music Awards, Mariah Carey was just 21 years old and still under the wing of first husband Tommy Mottola, who was notoriously controlling and likely had some influence over her style — which was very '90s, from her corkscrew curls to her brown-undertone lipstick. 

Post-divorce in 1998, Lanston points out that Carey "has more concealer on and a purple shadow that made her a 'Fantasy' to most men." She toned it down over time, and since the new millennium has linked up with makeup artist Kristofer Buckle. Her now-trademark look is just a step beyond natural and never appears overdone, featuring lush lashes, golden hair, neutral lips, and sculpted, glowing skin, which Lanston notes is "very clean, age-appropriate, and rosy-gold, especially her cheeks."

Buckle told The Hollywood Reporter of Carey's signature preternaturally pretty look, "I always approach in a very iconic kind of way to keep her very consistent, so if you're expecting Mariah Carey to walk in the room, you're getting exactly what you want."

What a girl wants is more makeup! Christina Aguilera evolved from frosty eyes and a fresh face in 1999 to Dee Snider in 2001 to her "Dirrty" period in 2003 and looked like an almost totally different person each time. For her Back To Basics and Burlesque era in 2010, she opted for an Old Hollywood glamour. Lanston told me, "The classic look always looks best on her: the red lip, winged eye, and white shadow."

Still, that doesn't mean she won't stray from it, as she did in late 2016 when she went for what Lanston describes as "a contour, highlight, and panstick with heavy lashes and a nude lip." It's a look that's actually reminiscent of fellow diva Mariah Carey, with whom she shares makeup artist Kristofer Buckle.

The Grammy winner's style varies in part just because she loves makeup so much. Buckle, told The Hollywood Reporter that the "Beautiful" singer loves playing with beauty products. "[Aguilera] will do anything — 'glue that on my forehead if it looks good,'" he said. "She loves experimenting and exposing herself through makeup."

Kim Kardashian has come a long way from organizing Paris Hilton's closet back in 2006. Lanston told us, "Nothing says assistant like a MAC blue black grey frosty eyeshadow."

By 2010, Kardashian became the face of contouring. Elena D, who studied under Kardashian's makeup artist, Mario Dedivanovic, told me, "Kim's looks through years is a journey through the contour, highlights, eyes, and lips. The first picture is a documentary of a weighty eye look, but Kim owned this smoky eye. In the second look, we see more solid foundation and played up sculpting. In the heavily contoured forehead and nose, and amped up cheekbones it is easy to recognize the future 'Contour Queen.' Kim's makeup artist, Mario Dedivanovic, is well known for making sculpting the face mainstream and her face is his canvas. In the third picture, she has a more feminine, not so made up feel to the makeup, while still playing with contour and light. The overall appearance of the look is cohesive and blended."

By 2017, Kardashian began a more low-key style. "The fourth look is a very contemporary look for Kim," Elena said. "Monochromatic, very light coverage and extremely well blended highlights and contours — technically mastered to perfection from Kim's makeup artist. The look is flawless and natural, enhancing her facial features, but still very exemplary of Mario's makeup style. Beautifully highlighted cheekbones and under eye area are a pleasure for the eye."

"From the first photo to the second picture it looks like a completely different person," Emmy-nominated makeup artist DeeDee Marcelli said of Kylie Jenner. In 2010, preteen Jenner "obviously wore much less makeup! You can see her freckles on her nose and she has a soft natural brow," Marcelli said.

At the 2017 Met Gala, Jenner left little to no traces of what she looked like before. "In her second pic she looks pretty, but very painted," Marcelli told us. "The brows are too dark. When she changed her hair color, she should have softened the color of her brows. Her lips look fuller (perhaps overdrawn); her nose appears thinner, but that may be due to carefully placed contour and highlighting."

Jenner also confessed to getting lip injections after more than a year of speculation over her suspiciously thicker kisser, which also played a huge role in her transformation from tween cutie to pouty adult.

In 2004, Katy Perry was fresh-faced with just a hint of bronze shadow. By 2009, she was full-on glam with a bit of a Vargas-girl look: red lips, thick lashes, winged liner, polished skin, and pink cheeks. In 2017, she Witness singer ditched her signature black hair, bleaching it and buzzing most of it off, and went straight-up clownish with her cosmetics.

"Her first look is when she first started her career and she looks young, soft and natural," Marcelli said. "Katy's second look is fabulous! The perfect makeup! From the shimmering highlighter on her cheeks, to the layers of false lashes and then finishing it off with her bright red lip, this is the best makeup I have ever seen on her. But her third look is a total disaster. It's creative (I'll give her that!), but distracting. All of it is overpowering the beauty underneath."

In 2005, Rihanna was still a good girl who hadn't yet gone bad, and her makeup was as youthful as she was — she was just 17! Lanston says she likely used a highlight eyeshadow, subtle black eyeliner, and a pop of pink lip gloss, evoking the teen that she was, though it didn't work exactly perfectly. Los Angeles based makeup artist Valerie Vasquez pointed out, "At first she looks like a baby wearing too much makeup! The makeup is flawless, she just looks so young to have all that shimmer everywhere and beyond glossy lips."

In her 2011 Rated R era, Lanston gushed, "That red hair made me feel like she was the only girl in the world! The pink shadow and white highlight on the eyelid was a masterpiece." In 2017, RiRi toned her look down, with soft pinks on her eyes and lips and glowing skin, and seemingly much less product than we're used to seeing on her. 

Makeup artist Shara Strand told me that RiRi's looks seem to have evolved with her personality and comfort with her superstar status. "Rihanna's first picture is fresh and young beauty. She became 'Jessica Rabbit' as she hit stardom in the second photo, and arrived to an extremely relaxed and casual makeup look in the third."

As Angelina Jolie transformed from a Hollywood wild child to a humanitarian hero, her look matured from baby-faced and fresh to super-sophisticated, which Boychuk explains is because even in her darker days, she never quite overdid it.

"Although some looks have been considered extreme, she manages to pull them off with a minimalist balance," Boychuk said. "Angelina first opted for a Marilyn-inspired look by lightening her hair to a strawberry blonde and adding curls. Her barely-there makeup is achieved by sweeping a soft silver shadow on her lower lash line with a subdued grey shadow liner on her upper lid and one to two coats of mascara. For her complexion, she used a flat matte powdered finish — quite the opposite of the highlighted glow we see today."

"Her next look is pure '90s, with a slicked down pixie cut, ice blue shadow, bold winged liquid liner, bold brows, an ivory matte complexion, and a metallic mauve lip," Boychuk said. "Fast forward a few years to the Angelina we've come to know: she maintains her sex appeal by going with a rich chestnut hue and soft waves, glowing complexion, tight-lined black eyeliner, and a red lip that truly give us Old Hollywood vibes."

There's one particular standout feature for Jolie that's evolved over time, and it's not her infamous pout. "Something remarkable to note would be her brows," Mutchie said. "In the 1990s, it was stylish to over-pluck, and many people have not even been able to regrow their brows back!"

In 2006, Jessica Chastain rocked a barely-there look, but by 2017, she became a sophisticated, strawberry blonde icon. 

"She is such a cutie, and her natural hair color is beyond beautiful, but I just love this strawberry blonde she has now," Vasquez gushed. "Her eyes look so much better now without the black inner rims. I also dig the face makeup on the second look and the bold red lips are beautiful. She went from cute to sexy!"