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Miley Cyrus has never shied away from contrast, and perhaps nowhere is that truer than in her constantly changing fashion sense. From the earliest days of her Disney Channel fame through to her present status as a bold pop culture leader, she's always pushed boundaries and rewritten the rulebook on what it means to be a fashion trendsetter.
Instead of opting for a single style or image, Miley has constructed her brand on fluidity, sliding between sleek red carpet glamour, punk-rock rebellion, retro Americana, and sporty Y2K nostalgia. Her style is reminiscent of the numerous decades of her career, each defined by fearless experimentation and an aversion to being categorized.
Today, a mature woman with an incredible voice and even more incredible vision, she's a style icon who wears not to impress, but to express. With each outing, whether in a leather bodysuit or a suit, Miley employs fashion as a means of narrative, reminding us that style, like identity, need not remain single-file.
From stardom as a child to becoming an international icon, Miley Cyrus's journey has played out before the very eyes of the public. Despite being born into a famous family, it was her debut as the double-life pop icon in Hannah Montana (2006) that catapulted her to fame. But Miley has since far outgrown her Disney beginnings, establishing herself not only as a singer and actress, but also as a fierce voice in fashion.
Her fashion path mirrors her inner journey, transferring from glittering teen outfits to brazen, usually inciting expressions that reflect her feelings, convictions, and experiences. In a 2021 interview with Vogue, Miley equated fashion to emotional candor, calling it a means of "wearing your heart, your values, your identity."
Her inspiration lies in the uninhibited expression of childhood, when dressing up was a matter of comfort and instinct, rather than criticism. For Miley, dressing up is not about mere trends, but about being authentic about who she is on any given day. That raw honesty has become the core of her image, and she is as much a fashion chameleon as a musical one.
Disclaimer: This article contains the writer's opinion. Reader discretion is advised.
Here are the top 8 Miley Cyrus red carpet moments of all time
Miley Cyrus has never played it safe on the red carpet, and that's precisely what makes her performances so much more remarkable. Whether lowering jaws in daring punk-chic ensembles or sporting timeless old-Hollywood glamour, Miley Cyrus employs fashion as a raw vehicle for personal expression. Year after year, she's produced some truly unforgettable moments, pushing boundaries while still honoring style icons.
From scissor-sharp silhouettes to show-stopping cut-outs, her red carpet gowns reflect her maturity and her unstinting fearlessness. They're about statements, re-inventions, and possessing the sort of courage to mature in public. Here are eight of Miley Cyrus' most memorable red carpet moments that demonstrate her continued evolution and unapologetic self.
1) Miley Cyrus in Versace at The Daily Front Row's seventh annual fashion Los Angeles awards
Miley Cyrus performed in a show-stopping routine at The Daily Front Row's Seventh Annual Fashion Los Angeles Awards, debuting a daring new haircut that was the talk of the evening. Her freshly colored hair, dark brunette roots slowly merging into blonder tips, was a jaw-dropping departure from her past looks and added a fierce contrast to her outfit.
She accessorized with a body-hugging black Versace corset and a tight latex skirt, an outfit that was rockstar cool and high fashion, the height of her signature look. But Cyrus wanted more than just a style statement here. Her look at the ceremony was personally inspired, as she had come to honor someone responsible for helping shape her visual identity: her stylist and friend Bradley Kenneth.
The Music Stylist of the Year award was a richly deserved tribute to Kenneth's creative influence, and Cyrus's attendance was not so much celebrity sponsorship; it was an honest outpouring of admiration and pride.
Their extensive collaboration, built on trust, artistic vision, and mutual respect, added an emotional resonance to the stylish night, in which it was made clear that at the center of every legendary look is a partnership to be savored.
Read More: Dakota Johnson’s 6 most talked-about red carpet looks
2) Miley Cyrus in Maison Margiela at the Grammy Awards 2024
On the 2024 Grammys red carpet, Miley Cyrus delivered one of the evening's most show-stopping looks, one that polarized opinion but also marked her long-standing love of defiant self-expression. Rather than wearing something conservatively classic, Miley Cyrus put on a theatrical turn in a very detailed gold gown constructed of more than 14,000 safety pins.
The dress, which borrowed its inspiration from John Galliano's Fall 1997 collection, teetered on the edge of anarchy and haute couture, mirroring her resolve to overthrow the anticipated conventions of pop star beauty. The intricate construction of the dress gained both approval and stunned glances, and it was undoubtedly a fashion moment that would not be ignored.
She completed the look with mustard yellow Tabi heels, an unconventional addition that only served to augment the outfit's veneer of deliberate provocativeness. What actually propelled the look beyond its shock value, however, was the inspiration behind the details.
Her large, backcombed bouffant wasn't just a bold hair choice, it was a loving homage to the late, great Tina Turner. In recreating Turner's iconic appearance, Cyrus honored not just one of the most powerful performers in music but also the crossing of the generational gap between rock-and-roll icons and their modern genre-bending counterparts.
The look, as polarizing as it was, was itself a performance. With the cross-pollination of punk reference, retro aesthetic, and sincere tribute, Cyrus once more proved that she's not in this to play by the rules; she's in this to shatter the visual paradigm and revel in the loveliness of chaos.
3) Miley Cyrus in Gucci x Balenciaga at the LACMA Art+Film Gala
At the LACMA Art+Film Gala, Miley Cyrus not only appeared but dominated with a fashion gamble that shocked everyone. Styling an entire look from Gucci x Balenciaga's provocative collection, Cyrus made a style point that few would be bold enough to try. The focal point of the outfit was an hourglass-cut, sharply cut blazer, stridently emblazoned with logos and over-dressed in a brazen floral print that combined strangeness and glamour.
It was matched by second-skin legging boots that ran from toe to thigh, creating the illusion of one uninterrupted line and introducing sleek, futurist elements to the outfit. This was not for the fashion-phobic; it was high-concept, theatrical, and uncompromisingly brazen.
But Miley Cyrus, who has an ability to combine rockstar ruggedness and high-fashion glamour, did it with the assurance of one who knows how to put on clothes as an expression. Instead of merely going along with trends, she appears to enjoy remodeling them, again demonstrating that her style is as bold and surprising as her music.
Read More: 8 times Cannes red carpet went viral on social media
4) Miley Cyrus in Saint Laurent at the Spring-Summer Men's 2019 show
In a bewilderingly unusual appearance at fashion week, Miley Cyrus returned to the dark, rebellious look that defined her earliest inspirations, paying homage to the early-2000s indie sleaziness and raw rock chick sensibility. At Saint Laurent's show in Malibu, she combined seamlessly the grunge-driven look with a high-fashion sensibility.
She anchored the look with thickly torn-up black denim jeans and tough biker boots, evoking the carefree, wild origins of her music and fashion career. Rather than going for the laid-back and renegade, however, Miley Cyrus paired this with an elegant, Parisian-stamped touch in the shape of a smartly fitted blazer, celebrated for its timeless beauty and as an investment fashion piece.
This juxtaposition of tough streetwear with chic, streamlined outerwear created an energetic look that was at once retro and modern, showing how she keeps evolving her personal style while honoring the raucous origins that first placed her in the world of fashion.
5) Miley Cyrus in Valentino at the LA premiere of Isn’t It Romantic
Abstaining from her risk-taking and sometimes provocative gaze that has become her signature red carpet fashion, Miley Cyrus opted for a very romantic and feminine look at the premiere of Isn't It Romantic.
With the selection of a flowy, sheer Valentino gown, Cyrus revealed a fragile beauty light years from her customary tough-edged notion of chic. The layering of lovely folds and lightened quality of the dress gave her an almost fairy-tale look with an integration of old-school romance coupled with contemporary sophistication.
This stunningly gorgeous ensemble immediately catapulted her onto the global fashion stage, and she found herself on most best-dressed lists, altering the trajectory of her public fashion career.
So much more than a flash in the pan, Miley Cyrus's selection was a considerate and compassionate one and illustrated how her style could speak to her own personal history.
6) Miley Cyrus in a Custom Stella McCartney at the Met Gala 2018
On the 2018 Met Gala, an event historically well known for its over-the-top fashion commentary, with the 2018 edition having the theme of "Heavenly Bodies", Miley Cyrus made a lasting impression by redefining the traditional black dress in her very own unique way. In partnership with Stella McCartney, Miley debuted in a custom-designed silk dress that at first glance appeared deceptively plain but was irrepressibly captivating.
Whereas the melodramatic, overblown fashions of the Met Gala seem always calculated to make one gasp with horror or outrage, her gown was understated but lit up with a quiet sensuality.
What made her fashion so exceptional, though, was that she paired it with her unique personality, her understated, sophisticated jewelry pairing with the dress to perfection, while dozens of visible tattoos provided a tough counterpoint that drove home the reality of her rough-scrabble existence.
This blend of sophistication and playfulness was reflective of Miley's own personality, showing that beauty lies in simplicity if confidence and good self-knowledge are present. The outfit was nicely balanced between the loftier atmosphere of the event and her own sense of style, making her sophisticated but subtly brash.
7) Miley Cyrus in Alexandre Vauthier at the MTV VMAs in 2014
When Miley Cyrus turned up at the 2014 VMAs, she showed up with an entrance that took fashion to such limits of decadence. Wearing a sleek, spotless two-piece black leather outfit by Alexandre Vauthier Couture, her style was the ideal combination of hard and stunning, a representation of her transitional persona at the moment.
But it wasn't merely the hard style that was so transgressive that evening. Instead of taking it herself, Miley Cyrus took the opportunity to bring attention to a larger cause by allowing homeless youth Jesse Helt, who had spent several nights sleeping on the streets, to take the award in her place.
Her energetic speech on the Los Angeles homeless epidemic transformed a potentially clichéd celebrity moment into one of the most memorable and powerful performances of the evening, highlighting Cyrus's newfound passion for activism and using her voice to make a difference.
8) Miley Cyrus in Mugler at the MTV VMAs
As Miley Cyrus crossed the MTV VMA red carpet, she didn't just show up, she made a statement. Her 2020 red carpet style was a fashion-secrets lesson on how to make a bold statement when Miley Cyrus sported a sheer, almost-nothing-at-all black mesh mini dress by Mugler's Fall/Winter 2020 collection. The see-through mini dress, adorned with intricate embellishments, challenged the couture-provocation protocol.
Whereas others chose subtle, Miley Cyrus committed fully to dramatic glamour, adding opera-length gloves and a sparkly diamond choker to the ensemble that drew attention, and the paparazzi camera. It wasn't about being risqué; it was about owning the moment, in the way only Miley could do.
Read More: Blake Lively’s 6 most iconic Met Gala looks of all time
Miley Cyrus never has any trouble taking over the red carpet, so every look is a personal statement of bold self-expression. From haute couture to teetering on the edge of danger with sheer gowns, or reimagined vintage glamour through fresh vision, each of her fashion statements is anything but passive, i.e., they're deliberate, brazen, and often front-page-worthy.
Year after year, Miley Cyrus has shown us that for her, fashion is not just about attire; rather, it's about performance, announcement, and declaration of her ever-evolving identity. From saucy boldness to sharp razor-cut precision, her red carpet appearances capture the essence of an artist who never plays by the rules, and that is precisely why the world's eyes remain glued to her.
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