Miley Cyrus Has Had A Stunning Style Transformation

Though Miley Cyrus has been in the spotlight for decades, it's near impossible to sum up her style in one sentence. The singer and actor has undergone multiple fashion eras and has never been afraid to experiment with new aesthetics, inspiring us with her unwavering dedication to self-expression through clothing. "Fashion to me is kind of flipping yourself inside out. It's like wearing your heart, wearing your guts, wearing your values, wearing your identity, wearing your pain, wearing your joy," she told British Vogue. "It's just about expression and how you feel that day."

That refreshing fashion take has earned the star plenty of praise, including from her hairstylist Bob Recine. "A lot of celebrities are very concerned with their fixed image, but Miley is a chameleon ... She's a person who loves change, and she understands that fashion is only fashion if it changes," Recine told Harper's Bazaar. Cyrus' clothing evolution has repeatedly reflected her life's ups and downs, forming one of the most authentic and stunning style transformations we've seen on any celeb.

Miley Cyrus first made headlines as a Disney darling in 2006, the year "Hannah Montana" debuted. The young teen dressed her age and clearly paid attention to trends, as she hit the Teen Choice Awards red carpet in a turquoise dress with red polka dots over jeans: The divisive dress-over-pants style was a major Y2K staple. She added a string of beads around her neck, another trend of the time, and proved she knew how to put an outfit together when she matched her shoes to the red in her dress and necklace.

Cyrus was also on the trend train during a press event in 2006, and showed another side to her style while posing alongside her dad Billy Ray Cyrus. She wore a light brown, patterned blazer with long, bootcut jeans over a zip-up jacket. The combo appeared to be the star's youthful take on the Y2K workwear look, which became a popular trend again in spring 2025.

Now a massive star thanks to "Hannah Montana," Miley Cyrus' more girly, glam side came out in 2007. She walked the red carpet at the Teen Choice Awards in a light turquoise sequin dress with a pink floral design, plus gold heels that matched the hardware straps on her dress. She also showed her fun and flirty side at the American Music Awards, in a strapless red mini-dress with a layered, balloon-esque skirt, which she wore with bedazzled peep-toe heels.

Both looks were very in tune with the sparkly, youthful costumes she wore as Hannah Montana, although Cyrus later admitted a lot of the shiny, uber-feminine dresses from the early days of her career were an extension of the fictional popstar — not her. "From the time I was 11, it was, 'You're a pop star! That means you have to be blonde, and you have to have long hair, and you have to put on some glittery tight thing.' Meanwhile, I'm this fragile little girl playing a 16-year-old in a wig and a ton of makeup," she told Marie Claire.

In 2009, Miley Cyrus began to move away from sequins, glitter, and brightly colored pieces to carve out her own style niche. At the Grammys, she wore a long black dress with a floral rosette on her left shoulder. The gown was one of her most sophisticated outfits so far and made it clear she was ready introduce the world to Miley Cyrus, as opposed to her "Hannah Montana" character Miley Stewart. She was maturing before our eyes. 

Her Golden Globe Awards maxi dress gave us a similar vibe. Though Cyrus wouldn't stop playing Hannah Montana until 2011, the stunning light beige, strapless, Grecian-style garment was more understated than the vast majority of her character's looks, and showed the then-16-year-old in a more demure light.

But while the dresses were far from red carpet disasters, Cyrus later admitted she was no fan of her clothing choices around this time. "My least favorite look: Pretty much 2008-2013. The Grammys were rough and tough for me. Yoikes!" she told Cosmopolitan in 2017. She also threw some shade at herself while speaking to Marie Claire in 2015, admitting, "I had some shady wardrobe choices when I was about 16 to 18." But while older Cyrus was no fan, she was clearly taking fashion more seriously. In 2009, she launched her own fashion line in collaboration with Walmart.

Around 2010, we saw Miley Cyrus age up her wardrobe in a seriously dramatic way. She celebrated her 18th birthday by posing alongside Demi Moore in an all-black, leather-look crop top and pants that gave us a glimpse at the fashion-forward, edgy style she was starting to embrace. 

Cyrus continued to inch away from juvenile clothing while on stage at the MTV Europe Music Awards, wearing in a nude, satin bodysuit with silver embellishments that wouldn't have looked out of place at a Hannah Montana concert. But she added an unexpected twist by pairing it with black, lace-up, calf-high boots.

That same year, she starred in the rom-com "The Last Song" and fell in love (and broke up) with her co-star, Liam Hemsworth, which may have influenced her more mature fashion. She also dropped the more grown-up album "Can't Be Tamed," which represented her most obvious transitional chapter yet.

Miley Cyrus had officially left the Disney Channel behind by 2012, and she underwent quite the image overhaul, including making the leap from long to short hair. Early that year, her style leaned toward Old Hollywood glam. The beauty had her hair in a voluminous bob when she attended the Vanity Fair Oscars party and looked mature and elegant thanks to her red lip and long-sleeve, embellished, gray dress. 

She also wore a boho-esque black crop top and floaty skirt to the premiere of "The Hunger Games," admitting her choice was influenced by Liam Hemsworth, who she'd gotten back together with. "It was the night I wanted to look the way that I would think he would like. He really liked it," she told InStyle of the two-piece. But 2012 was a year of big change.

The star was still finding her footing with fashion and self-expression, and made a drastic change to her aesthetic later that year. She ditched the classic style for an edgier vibe and appeared at the iHeartRadio Music Festival with a bleach blond, long pixie cut in a bouffant. The "Party In The USA" hitmaker also gave us rockstar vibes in a high-necked black crop top and metallic, silver, high-waisted pencil skirt that showed just a sliver of her midriff. And Cyrus wasn't afraid to be bold with her accessories. She added a gold and leopard-print Moschino waist belt, which matched her platform pumps.

Miley Cyrus raised more than a few eyebrows in 2013, when she wore some risqué, boundary-pushing looks that marked a drastic new chapter in her style file. At the iHeartRadio Music Festival, she wore a white mesh dress with furry sleeves over black-and-white underwear and black nipple pasties. 

It was also the year of her notorious MTV Video Music Awards performance with Robin Thicke, where she twerked in a teddy bear bodysuit before removing it to reveal a nude, shiny crop top and short shorts. She later told Vogue the outfit was designed to represent a rebirth and noted, "The bear reminded me of myself for some reason, I thought it was beautiful."

The star knew she'd gotten the world's attention with her out-there fashion, too. "I feel like every girl is trying to have a beauty shot and prove that they're 'fashion.' But I can be in white leggings and a white sports bra and I'm on a whole other level of s*** that those girls don't even get yet because they don't know how to do it," she told Harper's Bazaar.

The "Wrecking Ball" singer later admitted she partly stirred up controversy to distance herself from "Hannah Montana." "I'm actually not an attention-seeking person, sitting here as a 30-year-old grown woman," she told British Vogue in 2023. "I was creating attention for myself because I was dividing myself from a character I had played."

Miley Cyrus' fashion saw another evolution in 2016 when she backed away from the super risqué ensembles and dived into vibrant, hippie chic looks. At a "Crisis in Six Scenes" press conference, she wore a multi-colored crochet vest and white pants decorated with doodles of dogs that wouldn't have been out of place in the '70s. She added a bold silver belt with brightly colored, oversized jewels.

Cyrus' street style had evolved too. The star arrived to "The Late Show With Stephen Colbert" in an another '70s-inspired ensemble. She wowed in high-waisted, bootcut jeans with a belt featuring a large red buckle, which she paired with a vintage-style floral shirt, a statement coat, and chunky black shoes. She sported the look around the time she confirmed she'd again reconciled with Liam Hemsworth.

The outfits fit her mantra that fashion doesn't have to be serious. "I think fashion is so fun. I think people take it so serious," Cyrus told The Kit in 2015. She also made no apologies for dressing flamboyantly. "I don't have to wake up and go work in a normal office. I'm able to be free," she said, championing the idea that people should dress how they please.

Tennessee native Miley Cyrus went back to her country roots in 2017. At the Billboard Music Awards, she wore a wide-brimmed hat with a white, off-the-shoulder crop top and matching, ripped jean shorts with western-inspired boots. She also pulled off double denim — a trend that's been everywhere in 2025 — at the MTV Video Music Awards in a bedazzled denim jacket, cut-off jean shorts, and a T-shirt tied at the waist. Her more down-to-earth, casual looks fit her music at the time, as she released the album "Younger Now," which had country, pop, and rock influences.

The "Malibu" singer told Harper's Bazaar U.K. she purposefully chooses clothing that fits the personal and professional moment she's in. "My physical appearance is always an extension of my creativity. I am very literal when it comes to externally representing the 'era,'" Cyrus said. 

The star explained to Billboard that she'd purposefully evolved out of the experimental style that accompanied her equally experimental 2015 album, "Miley Cyrus and Her Dead Petz." "I love talking to people, and I approach them in a normal, 'Don't treat me different, 'cause I'm not' way. That's what started this evolution for me, getting out of my 'Dead Petz' phase," she said. "People stare at me anyway, but people stare at me a lot when I'm dressed as a f***ing cat," Cyrus added.

By 2018, Miley Cyrus' style had changed yet again. After embracing western-wear pieces, she turned her attention toward elegant gowns. She wowed in a sophisticated, deep red dress with sheer sleeves and a sweetheart neckline at the Grammys. The gorgeous garment was one of her most traditional red carpet dresses in years, and may have been influenced by her relationship with Liam Hemsworth. The two married in late 2018. 

"My relationship is very special to me, it is my home," she told Vanity Fair. "I feel less misplaced when we are in the same room, no matter where that is, but just because something changes in my relationship doesn't mean something has to drastically change in my individuality." Later, however, a source claimed to People that Cyrus didn't feel like she could be herself with the actor. "She just got to the point where she didn't want to hold back about who she is. She wants to be true to herself. Being with Liam, this was just not possible," the source claimed. The two split for good in 2019, confirming their breakup just seven months after tying the knot. 

Cyrus also opted for an elegant gown at the Elton John AIDS Foundation Annual Academy Awards Viewing Party. She put her own spin on formalwear in a gown that was part pink satin and part silver sparkles. The dress was reminiscent of her "Hannah Montana" era, but felt more grown up and representative of the woman she'd become.

Miley Cyrus showed off another arrow in her fashion quiver in 2019, when she adopted a more rockstar-esque wardrobe, and was all about accessorizing with bold jewelry. Performing at the Glastonbury Festival in the U.K., she wore a white crop top with skin-tight black vinyl pants, featuring several gold buckles down her legs. She added plenty of mixed metal jewelry, including a gold chain belt and chunky chain bracelets, and wore her locks in a wet-look style. 

"This look became kind of a staple for this era," Cyrus told Vogue. The multi-hyphenate explained she'd planned to wear a top in the same material as the pants, but opted to stay in the tank top she arrived in because the matchy-matchy outfit looked inauthentic. Her turn back to confidence-building, bold pieces may have been influenced by her divorce from Liam Hemsworth.

Cyrus wore a similar style while performing at the iHeartRadio Music Festival, an outfit that gave us throwback vibes to her 18th birthday party crossed with a little Joan Jett. The all-black ensemble featured a criss-cross crop-top with leather-look pants and elbow-high gloves. She added stacks of gold bracelets and necklaces, with a chain hanging from her pants.

In 2021, Miley Cyrus went edgy in a different way, embracing high-fashion looks. She attended the LACMA Art+Film Gala in a head-to-toe multi-colored floral suit with attached shoes. She carried a small top-handle bag in the same print, while her white turtleneck and curly shag — one of her coolest award show hair looks of all time – added to her vintage '70s vibes. 

Cyrus was a little more cutting edge with her fashion while arriving at "Saturday Night Live" that year. She opted for a matchy-matchy again, this time wearing a blue and black jacket and skirt co-ord over a simple black top, which she paired with on trend, chunky, tall boots.

The star referenced her ever-evolving style in her 2023 interview with British Vogue, admitting each of her fashion chapters has related to the person she'd become. "When I get dressed, I try to kind of think like my inner child, and be genuine and authentic in whatever I'm wearing," she said.

2024 saw Miley Cyrus move towards big hair and glam, while also making a return to jaw-dropping, risqué garments. She attended the Grammys in a barely-there gold number that showed plenty of skin — and was one of Cyrus' most bangerz outfits – made entirely out of strategic beading. She added XXL locks, an unfortunately controversial look. Her hair stylist Bob Recine told People the style was inspired by Barbarella. "It had a '70s, Barbarella feel while still having a modern, punk edge. By creating big hair, while still leaving some of the teasing visible, it allows the look to maintain a fresh, sexy feeling," he said.

But while Cyrus' daring red carpet dress wasn't for everyone, she proved she still had her finger on the pulse with her streetwear. She was spotted in New York City in loose jeans, one of the biggest trends at the time. She added a double-breasted, shiny black coat, black boots, and was ahead of the fashion game in one of 2025's hottest accessories, chunky sunglasses.

Although Cyrus was still happy to create a spectacle for events, the star admitted her beauty and fashion aesthetic had become more stripped back. After turning 30 in 2023, she told Harper's Bazaar U.K., "[I] keep it simple [because] more isn't always better, it's only more." The hitmaker shared a similar sentiment with Harper's Bazaar the following year. Wearing a black sweater with minimal makeup, she told the outlet, "This is my vibe."

Miley Cyrus turned down the dial a little on out-there fashion in 2025. After years of embracing colorful, revealing, and bold looks, she attended the Oscars in a black halter-neck gown that was more refined than her past outfits. The floor-length gown flattered her figure and featured sequins over her torso. She added sheer, embroidered gloves to inject some of her personality into the monochrome ensemble. Cyrus proved she wasn't done blazing her own trail, though, as she dyed her brows bleach blond, which made her aesthetic feel more avantgarde.

That same night, she attended the Vanity Fair Oscars party in a strapless column dress, which featured zip detailing over the bodice. Though the garment was safe by her standards, Cyrus made it hers with another bangs transformation, adding controversial baby bangs, which elevated what could have otherwise been a boring look. Clearly, Cyrus isn't afraid to change things up to express herself. This fashionista is ever evolving, and we can't wait to see what experimental looks she'll wow us with next.