Celebrity Makeup Transformations That Completely Missed The Mark

When it comes to makeup trends, celebrities are the ones who usually dictate what is popular and what has gone out of style. In fact, reinventing their makeup style every year or two is the norm, especially for those who want to remain relevant in terms of beauty and style. And even though they are primarily actors or musicians, plenty of celebrities have dabbled in the beauty industry, whether that be through collaboration with big makeup names or by starting makeup brands of their own. 

While we absolutely encourage makeup transformations and experimenting with your look, some of the makeup eras these celebs got stuck in just weren't that good. From a raccoon smokey eye that definitely wasn't a one-time mistake to rocking concealer lips well after the early aughts — celebs are sometimes relatable humans prone to mistakes, and these repeated makeup fails prove it.

Former Disney Channel star Miley Cyrus has been in the spotlight for almost two decades, and during that time, we got to see her go through numerous makeup phases. However, one that we really hope she has gotten enough of is her bleached eyebrows — a look the "Hannah Montana" actor rocked during early award-show season in 2025. While Miley Cyrus has given us a bold eyebrow transformation over the years, we aren't huge fans of her bleached era, especially when paired with a dramatic eye look.

While Cyrus loves to experiment with her look, the pop star has admitted that makeup isn't a big passion of hers. "My stepdad asked me the other day, 'Why are you the only one without a makeup line?'" the "Flowers" singer revealed on "The Interview" podcast in 2025. "I was like, 'Cause that's not my passion.' He goes, 'That's the right answer.' And it made so much sense. It's like, 'I don't have a makeup line because I'm not a makeup artist.'"

Miley Cyrus definitely isn't the only Disney diva who had a questionable makeup era. Selena Gomez usually rocks picture-perfect makeup, but the "Only Murders in the Building" star also has some questionable choices in her portfolio. In fact, who could forget her 2018 Met Gala look, which featured a dark and moody eye, a super-dewy and tan base (a bit too dewy and tan if you ask us), and a nude lip. And when we say nude, we're pretty much thinking of the infamous Y2K concealer lips. In fact, the entire look Gomez opted for was bad, securing her a spot amongst the worst outfits in Met Gala history (they can't all be winners). Unfortunately, the ultra-nude lip look has made a few appearances throughout the years, but eventually Gomez embraced a more natural lip color.

And since this repeated faux pas, the "Lose You to Love Me" singer has become something of a makeup icon, partially thanks to her makeup brand Rare Beauty. "I've been in makeup since I was seven years old, and I feel like that kind of messed with me," she told the press in 2021, per People. "I had professionals doing my makeup and suddenly I looked 25 when I was 16 and it was crazy," she added. "And then I felt like I looked too young all the time ... It just made me question my own beauty for what it was." While we're all about experimenting and finding out what makeup suits you, concealer lips are definitely a look that simply makes anyone look unwell.

Ever since she was a teen, Kylie Jenner has been known for her makeup, and there is no denying how much her signature styles have influenced the cosmetics industry. During her King Kylie era, the reality television star was all about a full face of makeup: one that featured the classic Instagram brows, characterized by their blended square beginning and dark ends. In fact, brows at the time were fully filled in without leaving any spots of skin showing — and this is something we were all guilty of doing.

Luckily, Jenner's makeup has changed since, and while the star still looks stunning with a full-glam look, she embraces a more natural, no-makeup makeup style today. "I've changed my look a lot, I think that I'm into the more natural skin," Jenner admitted to Vogue in 2023. "I wear a lot less but I've accomplished the same, snatched look ... I feel like the majority of the time, I'm not wearing makeup because I always have an event or photo shoot," the reality star said, adding, "I love doing my own makeup because it's just very therapeutic for me. I love to zone out." And while makeup will forever be a part of the star's career — especially considering she founded Kylie Cosmetics — there's no denying that Kylie Jenner looks stunning without makeup.

Musician Ariana Grande found incredible success with her portrayal of Glinda in the 2024 fantasy musical "Wicked." The character had a major impact on the "Yes, And?" singer, so much so that Ariana Grande has given us numerous outfits that scream Glinda from "Wicked." Unfortunately, the character also influenced her makeup routine, as the pop star decided to ditch her dark eyebrows for a more muted and blond look.

"Glinda's makeup kinda made me transform my entire look and my entire relationship to makeup. I just love it so much," the star revealed in a behind-the-scenes "Wicked" feature in 2023. "There's no like thick eyeliner. There's no like heavy crease. It's just like really warm and open and pretty ... It's also just a more honest representation of what you look like. It's just like, 'Oh, this is an eye.'" While we love that the star embraced a more natural makeup look, we do wish she would go just a shade or two darker with her eyebrows — it would definitely help frame her eyes better!

Barbz know just how iconic the color hot pink has been in Nicki Minaj's career; however, looking at her go-to lips in the early 2010s, we can't help but slightly cringe at the dramatic and bright shade. "Color, color, color. When in doubt, add color. Then, add some more," the rapper told Teen Vogue in 2012. And while embracing a colorful look helped put the star at the center of attention at any event, a slightly darker pink lipstick would have been a much better choice. 

The "Starships" rapper was so obsessed with the color at the time that she even had her own Nicki's Viva Glam version at M.A.C. "The lipstick I created is my new signature — a fresh hot pink," she said. "I wanted a shade that would make girls stop to wonder, 'Would this look good on me?' before trying it on — and then fall in love with it." Unfortunately, we're not in love with this shade on the star, and we're glad she has moved on from it.

Mariah Carey is definitely not known for having a subtle style, and we love her for that. However, she can go overboard with false lashes, and often they look too heavy for her eyes. Last year, we already called fake eyelashes as being outdated and shared tips to maximize your natural lashes, but we don't expect Carey to follow suit. The diva has always been known for staying true to herself, and falsies are just a part of her lifestyle.

The "All I Want for Christmas Is You" singer has admitted that she is not a fan of mascara, which is probably why she prefers falsies. "I hate mascara. I never wear it," Carey revealed to Vogue in 2017. "Whenever a makeup artist tries to put it on me, I throw a fit. If you're not wearing a lot of makeup, you don't have to take a lot of it off. So, my goal is to wear the least amount of makeup possible so I don't have to steam my face and take it all off." We suppose falsies are easier to take off than mascara!

If there's one makeup item that Taylor Swift is known for, it's her bright-red lipstick. "So many people asking about this lipstick that Taylor wears all the time," her makeup artist Lorrie Turk shared on Instagram Stories in 2024 (via E! News). "It's NARS Morocco Lipstick. She's worn it for years." In fact, the musician's red lips are so beloved that even we wore Taylor Swift's signature lipstick for a week to see what would happen.

However, the "Shake It Off" singer also went through a dark-red-lip era during the second half of the 2010s; it was so dark that it even put gothic makeup to shame. And while her "Reputation" era remains iconic, the super-dark shade of lipstick that accompanied it is a look we hope she doesn't bring back. With her fair skin and soft features, the dark color was just too contrasting. 

A major part of Katy Perry's appeal during her breakthrough in the late 2000s was her colorful and fun style. And while the star remains loyal to being expressive and using fashion and makeup to have fun, some of her looks just weren't that great. In particular, in the second half of the 2010s, the "California Gurls" singer had a tendency to go overboard with color when picking her makeup looks, and the result was often an incohesive mishmash of bold eyeshadows, lipstick, eyeliner, and even face jewels. Luckily, Perry has stopped going for a "more is more" approach when choosing her makeup routine.

While this makeup era might be one Perry probably regrets, we have to admit that we admire her love for using makeup as a tool to express herself. "I love makeup's power to transform and empower," Perry told People in 2018. "It could be a day look gloss that you glam up with some glitter to go out. It's a little whisper of a lash to put new curtains on the windows to your soul." Katy Perry also looks flawless when going makeup-free, and we definitely love a diva who can pull off both.

Lady Gaga was never one to conform to trends — she was setting them instead. And when it comes to her makeup, it definitely plays a major role in her transformation from Stefani Germanotta to Lady Gaga. "I never felt beautiful, and I still have days that I don't feel beautiful," the star told Allure in 2019. "All of the insecurities that I've dealt with my whole life from being bullied when I was younger, they come right back up to bite me. Then I put makeup on, and before I know it I feel this superhero within. It gives me those wings to fly," the "Born This Way singer revealed. "When I became Lady Gaga when I was younger, it was because I discovered makeup. It means so much to me on a deep visceral level — the power of makeup to change how you feel when you're at your lowest."

Knowing just how huge of a role makeup plays in her artistic expression, we can't help but feel a bit disappointed that Lady Gaga hopped on the fluffy eyebrow trend that reigned supreme in the early 2020s. We get it — we're all guilty of soap brows styled dramatically upward — but most of us don't have a team of stylists and makeup artists to tell us that the look might be a bit too much. But as with all trends, this one has expired, and Gaga's brows aren't nearly as laminated today.

When it comes to pop divas redefining themselves, Christina Aguilera is definitely one who could easily hold a masterclass on the topic. "I've always been someone that obviously loves to experiment, loves theatrics, loves to create a storyline and play a character in a video or through stage. I'm a performer; that's who I am by nature," she told Paper in 2018.

Even though her early-aughts "Dirrty" era remains one of the most iconic pop-culture moments of the time, her messy Y2K makeup is a part of it that we don't remember fondly. From ultra-thin eyebrows and spider eyelashes to patchy blush and unblended icy-blue eyeshadow — the "What a Girl Wants" singer's makeup was all over the place. 

Once Bella Thorne said goodbye to her Disney image, the star's style was all about discovering what she likes. And while experimentation is a necessary step everyone should go for when exploring makeup, Thorne's makeup in the late 2010s was memorable for all the wrong reasons. Bold colors, glitter, and thick eyeliner were her signature makeup, which the star usually applied herself.

"Anytime I'm wearing makeup, just know that I'm doing it. I got dermatitis from working on a movie, and I'll never let that happen again. Especially on movies, they don't use the right products, and my skin is allergic to a bunch of stuff," the former Disney star revealed in 2017 (via Refinery29). The "Shake It Up" star can pull off dramatic makeup, but some of the looks she has given us were definitely taking it too far. Eyeliner that goes across your temples? There's truly no need for that.

Supermodel Tyra Banks was never one to shy away from a bold look, but her love for a smokey eye may have gone too far at one point. In the early 2010s, it almost seemed as if Banks was conducting a social experiment by trying to see how much black eyeshadow she could get away with around her eyes before someone pointed out that it looked ridiculous. Unfortunately, it doesn't seem like anyone told her that. In fact, the model attended the 2012 Moth Ball with hot-pink lipstick and an eyeshadow look that was clearly inspired by a raccoon.

Even though she has made some questionable makeup choices over the years, Banks has admitted that makeup played a major role in her success. "Without makeup, I would have never been a supermodel. I don't wake up with naturally sculpted cheekbones — I paint them on!" she said in 2014 (via ABC News). "I believe makeup is the great beauty equalizer."

Rihanna's impact on beauty and fashion is undeniable, and frankly, there isn't much that the star can do wrong in either field. As a major trendsetter — and the founder of Fenty Beauty — RiRi definitely knows a thing or two about makeup and the power it holds. " ... beauty was a natural fit because makeup is such a huge part of my career and image," the star told Essence in 2020. "I wanted to do a line for years, but it needed to be credible, something that industry pros and girls around the world would respect." Having said that, even the crème de la crème of the beauty industry isn't immune to bad makeup, and the "Diamonds" singer is undeniably proof of that.

In 2009 and 2010, RiRi — who was rocking a stunning undercut and blond hair — hopped on the under-eye baking trend. While light powder was supposed to set her concealer and prevent it from creasing, in flash photography, it looked simply too light for her skin tone. Since the early 2010s, the makeup industry has become a lot more inclusive when it comes to shade range, and Rihanna and Fenty Beauty were at the forefront of the change.

Now, for more on the rich and famous and their beauty routines, take a look at celebs whose makeup never left the '90s.