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.
Taylor Swift is getting increasingly fearless with her style. Makeup artist Elena D pointed out that just as much calculation goes into Swift’s beauty as her music, going all the way back to her country roots in 2008, with her then-signature ramen-noodle style curls and smoky eyes.
“Taylor’s makeup looks are always flawless and on trend, so cameras love her face. The makeup on each [look] is balanced and harmonious, working perfectly with her hairstyle. Focused on the eyes, the makeup from the first picture is soft with a very natural base and glossy lips, a cat eye complemented with medium volume lashes for a touch of glam, and warm lower lash eyeshadow to soften the overall look. The peachy blush is a beautiful reminder for her girly nature.”
Swift began really taking risks once she chopped off her hair in 2014 and started hanging out with her infamous supermodel-heavy squad. Makeup artist Chris Lanston noted, “She was bold with this cut, and she put on a red lip to prove it.” Swift opted for an even edgier style when she co-chaired the 2016 Met Gala, where she sported bleached hair and a plum lip. “I like that she took a risk here with platinum blond hair and a deep, rich vampire lip,” Lanston joked, “because we all know she is one.”
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.”
Time to rip off the band-aid: Kelly Osbourne used to be terrifying, and it was seemingly by design. In 2003, the celebuspawn’s harsh glittery black smoky eyes and overdrawn hot pink pout made her look like she lost a street fight with a stripper and completely obscured her pretty features.
She cleaned up her act, literally and figuratively, by 2016. Makeup artist, colorist, and hairstylist Michael Boychuk told me, “Kelly Osbourne has one of the most dramatic celebrity transformations, from goth to glam. Originally owning the gothic look with severe black glitter eyes, hot pink lipstick and accessories like cigarette earrings to her current glamorous, but still very Kelly Osbourne style. Her lavender locks and half shaved head still scream punk rock in the prettiest way paired with a classy wing-tipped eye with dramatic lashes and a gentle blush pink lip.”
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.”
Avril Lavigne is nothing if not consistent, but that doesn’t mean she can’t mix it up a little. In 2002, Lavigne’s hair was honey-brown and pin straight, with black liner along the inner rims of her blue eyes and a ton of mascara. At the 2006 Cannes Film Festival, Lanston said, “[Lavigne] looks a bit trailer park with the bleached hair and heavy eyeliner.”
At the 2013 iHeartRadio Music Festival, Lanston said, “She looks like she was going for a Bowie look with dark pink eyeshadow, plus a gold swipe on her cheek, just in case you didn’t notice her.” At the 2016 Grammys, she opted for dewy skin, thick liner, and big, blonde waves.
“I just love when someone has their ‘look’ and stays true to it,” Vazquez told us. “When it comes to Avril we can always count on long and blond. She’s tried different blondes, and honestly her current blonde is my favorite. Aside from the occasional rock n’ roll look, she has her signature black-rimmed eyes and glossy nude lips, though she’s on a thicker brows train as of late.”
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.”
In 2007, the tall, naturally blonde Khloé Kardashian seemed to be striving to fit in with her petite, brunette sisters. “The first look is very creamy pink and eyeliner all in the rims and says, ‘Kim, I’m coming for you,” Lanston told me. By May 2017, Khloé went back to her roots, and the results were stunning. “She looks like she is more confident with a buttercream lip and better lashes,” Lanston said. “The lighter hair makes her look softer also. The only Kardashian that looks good [blonde] is her.”
“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.
“The image on the right has fun, graphic pops of color on the eyes, not designed to necessarily enhance the eyes (though the blue does help her brown eye color stand out more),” makeup artist Mandie Mutchie told me. “Her lips are the main focus, though, and she has overdrawn her lips, which means that she lined them outside of where her actual lip line ends. It is amazing how much a millimeter or two can make a huge difference!”
Marcelli thinks Thorne may have done a bit more than just overline her lips, though, noting, “Her nose looks thinner in the second picture, and she may have had some Juvederm injected into her lips. They look much fuller.”
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.”
Beyoncé’s makeup looks have constantly been on trend, for better or for worse, and have evolved along with her career. In 2000 with Destiny’s Child, her look was highlighted before highlighting was a thing. At the Grammys in 2002, you can spot some subtle contouring (especially on her nose), along with eyeshadow to match her purple gown. At the 2007 Golden Globes, Queen Bey goes for the gold everywhere — her hair, her eyes, her gown. In 2016, the Lemonade singer went for subtle, with a cream lip, brushed brows, and subtle gold glitter accents on her eyelid, Lanston said.
There’s another element to Beyoncé’s cosmetic evolution that many may miss: Mutchie notes, “Beyoncé’s looks show an evolution of trends, and an evolution of success, both on her part and on behalf of her makeup artist, or even makeup technology. One of the things about the four images that stands out to me the most is the change of her foundation colors from less natural to more natural as you move from left to right. This could be because of what was available (as the availability of makeup shades for people of color has been embarrassingly behind the times), or her ability to hire better and better makeup artists.”
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.”
Ariana Grande’s look has grown up with her. In 2008, a then-15-year-old Grande kept is simple and cute. “This first picture is how little girls are supposed to look,” Vasquez told me. “Fresh faced and natural. It’s very age appropriate — simple eye makeup and a light lip gloss.”
By 2011, Grande sported mermaid-red hair for her role as Cat Valentine on iCarly. In 2014, Grande had what remains her signature look now, Vasquez said, consisting of bronze lids and skin, cat eye liner, thick lashes, and a berry lip.
Boychuk explained, “As she evolved as an artist, so did her look. She’s gone from sporting her natural dark brown curls and a signature red hue to her iconic half up, half down look. With the exception of trying a bolder lip every now and again, Ariana’s experimented very little with her overall red carpet makeup looks. Her flair for feline-femininity is showcased by her staple cat-eye, soft metallic gold eye shadow and a matte dusty rose lip.” As for her dramatically different skin tone? That’s makeup too, Boychuk says. “She’s warmed up her complexion and maintained an ever present glow with the assistance of a spray tan.”
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!”
Kristen Stewart’s usual staple was a smoky eye and subtle lips, as seen in 2007 at left, then at the 2009 MTV Video Music Awards, which Vasquez told us suits her beautifully. However, she’s been experimenting much more since her Twilight Saga days, opting for short hair and a wine lip at the 2015 Venice Film Festival. In 2016, she chopped off her hair and got really experimental with her eyes at the Cannes Film Festival, with a look not many can pull off.
“This last look is fun and beautiful on her,” Vasquez said. “Sometimes too much red or pink around the eyes can make you look sick, but I think she looks great.”
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!”
How to transform your own look
If you want to make a dramatic change to your own look, find one constant. Do you always rock a smoky eye? Swap it out for a red lip. Love vampy, darker looks? Try going for a glowing, highlighted look and pink gloss. If you’re like Lady Gaga, ditch your trademark accessory or style (in her case, giant shades) and let the world see your cute face, then jazz it up with funky jewels or false lashes!
The beauty of transforming your makeup is that if you decide you hate it, all it takes is a little face wash to undo it and go back to what makes you feel like the most comfortable, prettiest version of you.