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Miley Cyrus has lived many lives: child actor, country singer, pop sensation, the list is endless. In her career spanning over two decades, the only thing predictable about her fashion is its unpredictability. Cyrus's sartorial choice draws inspiration from her current artistic journey, whether it's her flowing gowns or sheer chain-link dresses and everything in between.
Working with her long-time stylist, Bradley Kenneth, the singer embraces fashion's potential to go beyond just simple outfits. Bold and unique, she expresses her spirited personality through designers like Thierry Mugler, Versace, and Bob Mackie. With bold hairdos and emphasis on smoky makeup, she creates an impact every time she steps onto a stage or a red carpet.
While Miley Cyrus' every public appearance is dissected by fashion critics and fans alike, we'll be discussing the 5 best looks that took the world by storm.
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Disclaimer: All opinions in this article belong solely to the writer.
From pop princess to edgy queen: Miley Cyrus's best fashion moments
1) 66th Grammy Awards, February 2024 (Bob Mackie minidress)
For the on-stage performance of her hit song Flowers at the Grammy awards, Miley Cyrus donned a metallic minidress by Bob Mackie. The dress seamlessly blended the classic elements of a pop star's stage fit, with its asymmetrical fringe hemline, a corset-style bust detailing and a body-hugging silhouette. The appearance showed of the singer's toned midriff.
The Hannah Montana actress let the bejewelled dress do the talking, pairing it with silver pumps and simple threader earrings. She wore her hair in big, voluminous waves, reminiscent of an 80s rockstar.
The Hollywood Reporter reported the singer bought the dress by paying an undisclosed amount for her private collection before it was due to be auctioned. The proceeds went to the MusiCares Foundation, an organization that helps up-and-coming artists in the industry.
Cyrus won her first-ever GRAMMY Award in 2024 for Best Pop Solo Performance and Record of the Year. During the on-stage performance, she changed the lyrics of her song mid-performance to "I just won my first Grammy!"
2) MTV Video Music Awards, August 2017 (August Getty Atelier playsuit)
Miley Cyrus took to the stage to perform her hit single Younger Now at the 2017 MTV VMAs in a look straight out of a retro fashion magazine. She created a buzz in her hot pink August Getty Atelier playsuit with orange highlights, a high-collar neckline, a bright, stone-studded belt with "M" embossed, and an orange scarf tied sailor-style around her neck.
The star's playful look was accessorized with pink cat-eye sunglasses and ballet flats. Her hair was styled in a 70s-inspired high ponytail, accentuated by a voluminous bouffant and a single strand of curled hair framing her face. She was nominated for Best Pop Video for her song Malibu.
3) Met Gala, May 2025 (Pieter Mulier black tailored two-piece)
Miley Cyrus pulled out all the stops at this year's Met Gala. For the theme "Superfine: Tailoring Black Style", celebrating black history and dandyism as a fashion era, the singer wore a custom Alaïa two-piece ensemble designed by Pieter Mulier. A bold, textured, and full-sleeved crop top accompanied a voluminous fishtail skirt, with the tastefully done cut-out making the statement piece sing.
She accompanied the outfit with Cartier accessories, a chunky gold multi-layered necklace, tiny gold hoops, and a classic pair of sunglasses. Her hair was slicked back and worn in a long ponytail braid, she embodied the theme while bringing her classic edginess to it.
4) MTV Video Music Awards, 2020 (Thierry Mugler sheer black dress)
If there's any outfit that sums up Miley Cyrus' bold fashion, it is this one. Dressed in a sheer dress with a thigh-high slit from the Mugler Fall 2020 collection, the singer graced the MTV VMAs red carpet with her classic rockstar aesthetic. Classic lace gloves and strappy black stilettos elevated the dress's mirror embellishments and off-the-shoulder silhouette.
The artist sported a blonde mullet and a bright red lip, providing a striking contrast to the all black ensemble. She leaned into the edginess with a statement chunky necklace and bold hoops by Loree Rodkin. Cyrus modified the outfit later that night for her memorable performance of Wrecking Ball.
5) Isn't It Romantic LA Premiere, February 2019 (Valentino gown)
Miley Cyrus is known for her versatility, and this Valentino (pre-fall 2019 collection) floor-length gown is a classic example. The dress, embellished with a dramatic cape, petal-like accents across the neckline, and tiered ruffles, elevated the floral theme of the rom-com premiere. Miley's classic, bold style came through in the see-through skirt detailing.
She wore her hair in a slicked-back ponytail and sported a bright red lip to match the dress. Her look was complete with chunky rings and the sparkly safety pin earrings from Adina Jewels. She attended the premiere in her then-partner Liam Hemsworth's stead, who couldn't make it due to health reasons.
Miley Cyrus creates viral moments with her bold and unique fashion, with fans left guessing what aesthetic she will embrace next.
