The Most Outdated Outfits Miley Cyrus Has Ever Worn

Global superstar Miley Cyrus is no stranger to eccentric fashion or, indeed, style controversies. Since her early days as a child star with a wholesome image, Cyrus has undergone a stunning style transformation that's not over yet. Her evolution seems constant and unending, vacillating between flawless haute couture and the completely unexpected — usually making no stops in between. Are certain ensembles challenging? Certainly. But while we can't forget some of Cyrus' most inappropriate outfits, we can at least give her credit for pushing the envelope. When you take a big swing, sometimes you get a big miss.

The "Flowers" singer hasn't always nailed the two ends of her personal style spectrum. Occasionally, even fashion-forward Cyrus has fallen prey to flash-in-the-pan fads, strange throwbacks, and ill-conceived statement looks. Alas, Miley Cyrus' most outdated outfits prove that no one is immune to the passage of time — or the inevitable embarrassment of outmoded trends.

Miley Cyrus' "Hannah Montana" era was iconic, and a big part of that was the star's then-trendy fashion. Looking back, her ensembles from this period are like a time capsule of early '00s style — nostalgic but ultimately out-of-date. Take, for example, her look while performing as Hannah Montana in the "Good Morning America" Summer Concert Series in 2007. It's all there: the long, sparkly tank top, the studded over-the-shirt belt, the white skinny jeans. This quintessential '00s look was perfect for the time, but now Cyrus can safely leave it in the past.

Featuring a long, tasseled kimono and flared jeans, Miley Cyrus' boho-lite look at the 2011 premiere of "Justin Bieber: Never Say Never" was, we're sorry to say, pedestrian. But we aren't the only ones who think so — Cyrus herself called out the throwback outfit as one of her all-time worst. As the "Wrecking Ball" singer told Marie Claire, "I had some shady wardrobe choices when I was about 16 to 18. I wore this hippie outfit ... that I'm like, 'Girl, who told you — it was not Woodstock, it was a premiere.'"

Not to pick on 2011 Miley Cyrus, but her hippie look wasn't the year's only outfit with a short sell-by date. Attending the Grammys, Cyrus opted for a Roberto Cavalli gown that embodied every of-the-moment pop-rock trend of the age — tiger stripes, sequins, wrist cuffs, the whole shebang. The busy ensemble was more akin to an expensive version of the then-best-selling styles from Kohl's. What's more, Cyrus wore this dress twice, having already donned the glitzy look while posing for a Marie Claire cover. We'll give her this: She was dedicated to the trend.

The Met Gala is all about fashion experimentation, so we try not to judge the looks too harshly. That said, we weren't — and still aren't — fans of Miley Cyrus' interpretation of the 2013 theme, "Punk: Chaos to Couture." Everything about the look is blunt and dated, its styling somewhere between '80s stereotype and noughties kitsch. The gown's chunky, seamed mesh overlay could have come from Hot Topic, the bird's nest of Cyrus' hair was too on-the-nose, and the bleached tips against dark roots were uncomfortably close to feeling frosted.

Oversized silhouettes have been in vogue for years, and there are ways to rock the oversized trend for petite heights like Miley Cyrus' 5'4" frame. But in 2018, Cyrus donned a pair of baggy plaid separates that still felt like a miss. The drab print had distinct pajama vibes, and Cyrus' accessorizing gave late '90s with the chain necklaces, creepers, and Jamiroquai-worthy furry hat. We love a '90s throwback as much as the next person, but this look needed a fresh twist to make it feel more contemporary and less antiquated.

Usually, Miley Cyrus' avant-garde fashion sense is more out there than outdated. But her 'fit at the 2024 Grammys — which could have been spectacular with the right styling — felt like another disjointed mishmash of historical periods. Taken on its own, Cyrus' skin-baring Maison Margiela dress is interesting. Constructed entirely of gold safety pins, its intricate design feels worthy of a modern Cleopatra. But this daring dress is made costumey by Cyrus' velvet tabi heels and bizarre '80s hairstyle, which looks better suited to the "Golden Girls" than an award-winning pop star.