Miley Cyrus’ Style Evolution Is Everything: Check Out Her Most Iconic Looks Through the Years

If there’s anyone in Hollywood who’s transformed when it comes to their personal style, it’s Miley Cyrus. The “Slide Away” singer has had her fair share of different looks over the years, constantly reinventing herself. From her innocent Disney days to her more adult, risqué style, we’ve covered it all.

As it happens, Miley has opened up on a number of occasions about what it was like to break out of her cookie-cutter — ahem, Hannah Montana — mold. “I did once I was 18 because it felt ridiculous,” she told Elle magazine of her decision to leave the series that made her a bona fide star.

“The minute I had 𝑠e𝑥, I was kind of like, I can’t put the f–king wig on again,” Miley continued in the July 2019 interview. “It got weird. It just felt like … I was grown-up.” Grown-up, indeed! So much so, that her style drastically changed afterward. Fans will never forget her wildest looks, like when she twerked on Robin Thicke while wearing a peach latex bikini at the VMAs in 2013, or when she went fully nude for the “Wrecking Ball” music video the same year.

Her sense of style has been daring ever since, but recently she’s taken a more rock n’ roll turn. After dropping her Plastic Hearts album in 2020, she began sporting a Joan Jett-esque mullet and ’80s punk-inspired clothes. One of her most iconic looks of 2020 was the leather outfit she wore for her New Year’s Eve performance. The studded matching set featured a black bralette and tight pants, plus tall leather gloves and strappy pumps.

But that doesn’t mean she has the rock n’ roll lifestyle to match. In fact, Miley opened up about ditching her partying ways in 2020. “I’m sober,” she told Joe Rogan during a visit to his podcast in September 2020. “I learned so much about all the effects, which again, you’re not really taught. It’s not really the drinking, it’s the staying up all night, and once you have your drink, you end up smoking. It’s really just a personal preference, I think everyone should experiment. … You learn a lot about yourself and the people around you.”

We can’t wait to see what over the top outfit she’ll choose next!

Scroll through the gallery below to see Miley’s complete style evolution over the years. 

Ron Galella, Ltd/WireImage

1994

Miley and her dad, Billy Ray Cyrus, were fashion icons way before starring on Disney Channel’s Hannah Montana. We love his mullet and her curls — so ’90s!

Lawrence Lucier/FilmMagic

2006

A 13-year-old Miley showed off her pearly whites ahead of the Hannah Montana premiere date in March 2006. So young!

Jeffrey Mayer/WireImage

2006

Only two months later and the brunette beauty began experimenting more with makeup. We’re so here for that gloss!

Peter Kramer/Getty Images

2006

In June 2006, Miley made an appearance at MTV’s TRL rockin’ a casual outfit with some cute white heels.

Kevin Winter/Getty Images for Radio Disney

2006

The blonde wig is hands-down of her most classic looks! She’s not even 14 years old in this photo, but she was already an established pop star.

Jeffrey Mayer/Jeffrey Mayer

2007

In August 2007, the Disney alum attended the Teen Choice Awards in a stunning mid-length summer dress. This was also one of the last times she rocked her dark brown locks for a while.

Jon Kopaloff/FilmMagic

2007

A 15-year-old Miley traded in her dark tresses for lighter ones. This was the first time she started to experiment with her style on a larger scale. So subtle compared to the later years, right?

Lester Cohen/WireImage

2008

For the Hannah Montana & Miley Cyrus: Best of Both Worlds concert film premiere in January 2008, the performer sported a much darker look than she had before by dying her hair black.

2008

By April 2008, she was back with light-toned hair and a pretty flowy dress that showed off her girly side.

David Aguilera/BuzzFoto/FilmMagic

2009

Exactly a year later, she added hints of blonde to her hair. While we love her red carpet style, Miley’s street style is one of our faves — so casual and cute.

Christopher Peterson/BuzzFoto/FilmMagic

2009

There are so many things we love about this outfit — the bold leggings, the fact that she’s missing a shoe, but our fave has to be the Jonas Brothers graphic T-shirt. Yup, she’s one of us.

2010

The Disney alum looked like an absolute princess at the 2010 Oscars. This dress fit her like a glove.

Kelsey McNeal/ABC via Getty Images

2010

It wasn’t long until Miley began showcasing her more adult side. For a Dancing With the Stars performance in May 2010, she performed “Can’t Be Tamed” and dressed to the theme of the provocative music video.

2012

If there’s one thing The Last Song star is known for, it’s her versatility. For the 2012 People’s Choice Awards, she dressed like a total girly-girl.

2012

The following month, she gave old Hollywood vibes in this lengthy gray gown. To make her look pop, she added a red lip, which is always the answer!

Isaac Brekken/Getty Images for Clear Channel

2012

Seven months later, she unleashed her rocker side with Jon Bon Jovi as she flaunted her newly dyed short ‘do.

Rabbani and Solimene Photography/WireImage

2016

In May 2016, Miley sported a spikier version of her pixie cut. Here she began showing she doesn’t care what anyone else thinks and we love her for it!

Kevin Mazur/MG18/Getty Images for The Met Museum/Vogue

2018

Fast forward to the 2018 Met Gala and she’s back to the basics with hair that resembles her earlier days. Her signature waves are too gorgeous!

Axelle/Bauer-Griffin/FilmMagic

2019

In 2019, she opted for bangs making us more nostalgic for her Disney days.

Kevin Tachman/MG19/Getty Images for The Met Museum/Vogue

2019

Miley wore a glittery dress in honor of the Camp theme at the 2019 Met Gala. This may be our fave look ever considering she pretty much dressed up like Hannah Montana. Her MIND!

Gilles Mingasson/ABC/Shutterstock

2020

Miley tore up the stage at Dick Clark’s New Year’s Rockin’ Eve on December 31, 2020, putting her new rock n’ roll mullet on full display.

2021

Balenciaga mama! The “Wrecking Ball” singer brought puck and floral galore while attending the LACMA: Art and Film Gala in November 2021.

She wore a Gucci x Balenciaga Hacker Project suit with a matching mini-handbag.

Photo by Jordan Strauss/Invision/AP/Shutterstock

2021

When they were just friends! Miley gave ‘60s realness at the Gucci Love Parade fashion show in Los Angeles. She posed for a picture with now-boyfriend Maxx Morando.

Mega

2022

Grocery store fit check! The Hannah Montana actress sported an all-black ensemble while grocery shopping with mom Tish Cyrus at Erewhon Market in Los Angeles.

She wore a black casual jumpsuit and cropped black blazer with total ‘80s shoulders.

Alberto Valdes/EPA-EFE/Shutterstock

2022

Miley took the stage at Lollapalooza in an edgy metallic blue catsuit in Santiago, Chile.

26 of 27

Richard Young/Shutterstock

2023

The “Flowers” artist rocked a two-toned Versace gown to the designer’s Los Angeles fashion show in March 2023.

Source: lifeandstylemag.com

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