When it comes to breaking fashion norms, you can count on Miley Cyrus to come in like a wrecking ball. Born Destiny Hope Cyrus, the star has presented a stunning evolution from the trendy outfits of her young teenage years to her jaw-dropping looks on today’s red carpet. While some could see Cyrus’s choices as clashing with each other, the pop star continually presents daring transformations, provokes fashion norms and makes bold aesthetic statements.

Cyrus was catapulted into acting fame with her hit lead role as famous pop star Hannah Montana. At her first red carpet for Disney in 2006, Cyrus appeared in a suit jacket and skinny jeans, reminiscent of the period trend to wear business casual attire everywhere. Cyrus could also be seen in layered tanks, chunky belts and denim for much of her character as Hannah Montana, though this wardrobe was almost certainly not of her choosing. 

At the 2006 Teen Choice Awards, Cyrus wore a blue dress with polka dots over skinny jeans, following the ’00s trend to wear dresses over jeans — a pairing that is on the rise again. During the early 2000s, it was also imperative to bedazzle every outfit. Cyrus followed suit, appearing in sequined dresses twice in a row for the Teen Choice Awards. 

These early outfits were likely shaped by her young age and the pressure to conform to her identity as Hannah Montana. As Cyrus grew older and broke out of her role of Hannah Montana, she began to assert her own style.

In 2009, Cyrus released “The Time Of Our Lives,” her first EP and critically dubbed “step into adulthood.” In her performance of “Party in the USA” at that year’s Teen Choice Awards, Cyrus appeared in a black vest, shorts and boots — a hint of the punk-rock, edgier style to come. 

The release of her fourth studio album, “Bangerz,” flipped the script in Cyrus’s style. The album included hip-hop elements and identified more with how Cyrus felt at the time: “disconnected” from the music she had released in her teens. This marked change was certainly also reflected in her looks. 

Cyrus chopped her hair into a blonde pompadour haircut, a far cry from the long brunette ringlets she wore for her looks as a Disney Channel star. In her acceptance of the Choice Style Icon Award, Cyrus appeared in a sheer black blouse, leather bra and miniskirt by Saint Laurent.

The VMAs in 2013 were a controversial moment for Cyrus, as twerking on Robin Thicke seemed to viciously separate her from her adolescent image as Hannah Montana. While Cyrus suffered much criticism for the move, it also gave her the freedom to push boundaries and transform her own style. 

Cyrus continued to appear in fantastical and outrageous looks during the release of  “Miley Cyrus and Her Dead Petz” in 2015, her fifth studio album with psychedelic-pop undertones. 

The signature bright tones of psychedelic fashion appeared in a revealing look from Simone Harouche for the 2015 MTV Music Awards. She also wore a barely-there silver ensemble by Versace, signifying her freedom, for the 2015 VMAs. In an overstep of the creative fashion process, Cyrus also adopted culturally appropriative faux locs, a protective hairstyle used by Black communities. She apologized for this and other diminutive comments towards rap in 2019. 

Mimicking her return to her country-pop roots in 2017 with the music of “Younger Now,” Cyrus reinstated natural blonde locks and wore more muted colors and styles. Among these was the two-color Prabal Gurung dress she wore for the 2018 Vanity Fair Oscar Party. 

However, Cyrus did not forget about the rock elements in this album. She mixed country and rock with her 2017 VMAs appearance, donning a matching set of bright blue and studded leather bell bottoms and a cropped jacket. 

Leading to the release of her 2020 studio album “Plastic Hearts,” her gateway into pure rock, Cyrus maintained maturity and edginess by crossing punk-rock outfits with couture. In the Saint Laurent show for 2019, she wore ripped pants, a dark-gray blazer and layered necklaces. By then, Cyrus had also taken on her iconic wet-look hairstyle with blunt bangs. 

Moving forward, Cyrus has added a level of sophistication to her edgy outfits, namely by mixing eighties pastel or traditionally menswear-inspired elements. For example, she wore a slightly oversized floral Balenciaga x Gucci suit with a pink lip at the LACMA Film + Art Gala in November 2021. 

With the release of her most recent single “Flowers” this year, ahead of her upcoming album “Endless Summer Vacation,” fans are sure to delight in her next possible fashion transformation. In the music video, Cyrus wore an archival Saint Laurent gold lame dress from the 1991 Fall/Winter collection contrasted with an androgynous suit from the 2022 Fall/Winter collection. These outfits likely imply Cyrus will continue to wear bold and vibrant looks, but they’ll be drawn from archival collections and appear in classic cuts (as opposed to the shiny bodysuits of before).

Based on the initial album trailer for “Endless Summer Vacation,” which appears to heavily feature a mix of rock and synth pop and a monologue reminiscent of Lana Del Rey or Halsey, Cyrus is sure to appear in more rocker style looks and vintage pieces. However, it is difficult to predict her fashion choices — Cyrus’s ability to stun audiences lies in keeping fans guessing.