Miley Cyrus' Biggest Makeup Mistakes

Miley Cyrus has earned her pop star title, and the same cannot be said for many celebs these days. The actor and singer-songwriter has long been a part of the entertainment world, having undergone a stunning style transformation over the years. Indeed, A-list celebs are expected to look the part, which is why it feels so jarring when they make mistakes that remind us of their mere mortal condition. While dramatic looks come with the territory, the "Flowers" singer is not immune to the occasional makeup miscalculation.

Cyrus has embraced her celebrity status, successfully transitioning from child actor to Disney singer, and now she's a full-fledged artist. Therefore, it's understandable for her loyal fan base to hold her to certain standards, especially for those who grew up watching her on "Hannah Montana" where her screen-ready skin remained nothing short of perfect. The young star proves no exception here, as she's been caught sporting several questionable looks, including the heavily publicized powder incident and her experimental eyeshadow, to name a few.

In May 2013, Miley Cyrus attended a party in Hollywood where she was labeled the hottest woman of the year. She marked the occasion with an unfortunate red carpet photo that revealed a layer of unblended powder below her chin. The powder incident was all everyone could talk about and she eventually addressed the embarrassing moment. "I've done the joker, you know where you get the white powder and it looks insane. It was on the red carpet," she told E! News. "It was getting Maxim's hottest whatever of the year and I looked insane."

Everyone loves a pop of color, but there's no harm in admitting that there is a time and place for experimenting with cute colors, and the 2019 MusiCare Awards isn't one of them. Haphazardly swiping on the first color she saw in her eyeshadow palette doesn't complement her outfit as well as Miley Cyrus might have hoped. Instead, the lavender eyeshadow and peach-pink lipstick feels like a combination a young girl playing with her makeup set would wear. Her all-black ensemble deserved something more sophisticated — and this wasn't it.

Soaking in the sun to get a golden tan is all fun and games until you forget to balance out the bronze tones while applying other products. The "Party in the USA" artist fell for this very trap when she swiped on a barely there shade of lipstick ahead of the 2013 Pre-Grammy Gala. This one-tone look veered too close to the early 2000s concealer lips trend for our liking. We did see an upgrade for the concealer lip craze in 2023, but the bizarre beauty fad was considered outdated in 2013.

At the 2021 Art+Film Gala in Los Angeles, the "We Can't Stop" singer donned a playful Gucci x Balenciaga suit with tropical colors and matching accessories. We love her choice of lipstick here, which falls in between coral and peach fuzz, but she lost us with the powder-blue eyeshadow. Miley Cyrus stepped out of time with this bold look due to the heavy pastel eyeshadow, coral lip, and the bleach-blond shag cut to boot. The ode to the '80s is always fun, but she could have modernized the eyeshadow and created more depth.

At the 2019 Vanity Fair Oscars Party, Miley Cyrus wore a gorgeous black sequin dress that featured a plunging neckline and a snake lariat necklace with emerald beads. Her makeup artist did a wonderful job with the subtle matte finish, but it lacked zhuzh. For her vampy ensemble, a classic scarlet or ruby-red lippy would have done well here, rather than the muted pink. The overall vision is clear, as the soft shade helps balance the deep emerald and black, but even a darker latte lip with some gloss would have done a better job at elevating the look.