Miley Cyrus' Biggest Makeup Fails Of All Time

As a quintessential child-star-turned-superstar, Miley Cyrus has spent quite a bit of time in the public eye. And like many musicians, she has been unafraid to experiment with different styles throughout her career. In fact, there have been multiple times Cyrus was unrecognizable after pulling off a dramatic transformation. Because of this, it actually comes as a surprise just how few makeup mishaps she has had over her nearly two decades in the spotlight. The star has stayed fairly consistent with her beauty looks through her many eras and styles. Of course, no amount of good taste and skills can prevent someone who attends tons of public events from having a makeup flop now and then. And, this is true for Cyrus, too. 

Cyrus may be better known for her controversial outfits, but she has equally worn some makeup looks that have been just as bad as her whackiest ensembles. From heavy eyeshadow to washed out, monochromatic cheeks and the eyeliner choice that sparked many memes, her most notable makeup errors have been all over the map. These five looks are proof that even the most stunning stars have bad makeup days from time to time.

Sometimes the wrong lighting can change your makeup from flawless to a total faux pas. This is something Miley Cyrus knows firsthand. In 2013, the star headed to Maxim's Hot 100 party sporting a Valentino jumpsuit and a bold red lip. Unfortunately, while she was on the red carpet, the white powder she had on her chin and below her cheekbones looked extra apparent. We've seen this particular makeup fail happen with other celebs; bright lights and flash photography can enhance white powder. Evidently, though, it's still a major makeup mistake.

More often than not, Miley Cyrus' makeup looks are minimal and natural. In particular, she tends to go light on her eyeshadow. However, when she attended the Versace Fall 2023 Fashion Show, the star switched things up and packed a punch with a dark smokey eye. Unfortunately, not only was this eye makeup a bit too heavy for her deep set lids, it also created high contrast against her particularly light, flat foundation. This left Cyrus looking ghostly and almost unrecognizable. 

In 2013, Miley Cyrus attended the "Paranoia" LA premiere with a short and sleek haircut and a simple makeup look. Unfortunately, the products she used for this look left her looking all wrong. For starters, clumpy mascara left her with some serious spider lashes. Her nude lip was also too opaque and light. Pairing this with flat, minimal foundation and barely any blush or contour made her appear washed out and unfinished, rather than fitting the clean girl aesthetic she may have been aiming for. 

Over the years, Miley Cyrus has sported some very natural-looking lash extensions. The singer's love of a subtler lash made it all the more surprising when she showed up to VH1 Divas 2012 with a total eyelash overload. The star wore some seriously long, voluminous falsies that totally took over her face. What's more, in many photos from the event, the lashes looked messy and artificial — likely because they were oversized. They dark lashes stood out even more thanks to her otherwise monochromatic makeup and bleach-blond pixie cut.  

By now, we all know the photo of Cyrus at the 2008 Grammys that inspired many memes for years to come. Interestingly, this makeup look was a standout from the others she has worn over the years — and not for a good reason. Her eyes were lined all the way around with black eyeliner, which caused them to appear smaller and close together. This is part of what gave Cyrus the odd stare that took the internet by storm. The darkness was exacerbated by her pale nude lip and light-colored eye shadow.