Miley Cyrus’ Shocking Red Carpet Style Evolution

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Before Miley Cyrus debuted her controversial look and twerking moves that even got singer-songwriter Sinéad O’Connor writing her fifth open letter (seriously, guys, give it a rest already), the former Disney star actually had red carpet moments worth revisiting. From one of her first appearances as a giggly little girl to her transformation as a full-fledged artist with a style of her own, there is no doubt that Miley has picked up a thing or two about fashion in her highly-publicized journey as an artist.

We’re revisiting Miley Cyrus’ humble beginnings and counting down 22 of her note-worthy red carpet frock looks.

1. May 23, 2006

Miley Cyrus

Billy Ray Cyrus and daughter Miley CyrusBilly Ray Cyrus and daughter Miley Cyrus 41st Annual Academy of Country Music Awards in Las Vegas on May 23, 2006

Miley shared the red carpet with dad Billy Ray Cyrus at the 41st Annual Academy of Country Music Awards which was held at the MGM Garden Arena in Las Vegas. Miley sported a fully beaded ruffled dress and silver heels.

2. November 21, 2006

Miley Cyrus

Miley had her first bohemian look when she turned up at the American Music Awards 2006 at The Shrine Auditorium in Los Angeles wearing a white dress with feathers and silver embellishments. Mommy Tish makes a cameo behind her.

3. January 9, 2007

Miley CyrusA more sophisticated look was seen from Miley at the 2007 People’s Choice Awards at the Shrine Auditorium in Los Angeles. The child actress wore a ruched metallic green tube dress and silver heels.

4. November 18, 2007

Miley Cyrus Fashion Evolution 5Miley has definitely been seeing herself more as a woman when she started embracing her curves in a red mini dress at the 2007 American Music Awards held at the at the Nokia Theatre  in Los Angeles. The singer took to a gold Rebecca Minkoff clutch to polish off her look.

5. February 24, 2008

Miley Cyrus

Miley CyrusMiley makes her first appearance on the red carpet of the 80th Annual Academy Awards (Oscars) in Los Angeles wearing a form-fitting, full-length Valentino in its iconic red shade, and accessorizing with a bronze Mary Norton lizard clutch.

6. September 7, 2008

Katy Perry and Miley CyrusMiley busts out a huge grin as she held hands with Katy Perry for a photo op at the 2008 MTV Video Music Awards in
Los Angeles. Miley wore a sequined, ruffled dress in navy blue paired with black cutout heels.

7. February 7, 2009

Miley Cyrus

Miley CyrusThere is clearly some style experimentation taking place as the Disney star chose a unique printed drop waist dress with a few good layers of ruffles at the back. Miley attended the annual pre-Grammy gala in Beverly Hills, which was hosted by Clive Davis and The Recording Academy.

8. February 9, 2009

Miley Cyrus

Miley CyrusAnother couture moment was born when Miley slipped into a black full-length Hervé Léger for the 51st Annual Grammy Awards held at the Staples Center in Los Angeles. The dress had beautiful bandage details on the torso, accented by an embellished rose and a soft cutout at the back.

9. February 22, 2009

Miley Cyrus

Miley CyrusOne of Miley’s most memorable red carpet looks was born at the 81st Annual Academy Awards (Oscars) at the Kodak Theatre in Hollywood. The singer-actress dressed herself in an ethereal Zuhair Murad creation,  which she accessorized with a gold Mary Norton clutch, BCBG shoes, and Neil Jane jewelry.

10. April 23, 2009


hanna_montana_01The Hannah Montana craze continues as the film officially made its UK premiere at the Odeon West End in London. Miley wore a stunning mini from Hervé Léger by Max Azria  (Fall 2009 collection), which she paired with charcoal gray Sergio Rossi pumps.

11. May 31, 2009

Miley Cyrus

Miley CyrusMiley Cyrus channeled a Jennifer Lawrence look even before Jennifer Lawrence became an it-girl. Miley went through a nude phase in a short halter dress with a draped front at the 2009 MTV Movie Awards held at the Gibson Amphitheatre in Los Angeles, California.

12. January 31, 2010

Miley CyrusMiley let her personality shine through in a dress from Hervé Léger  by Max Azria (Spring 2010 collection), which she wore to the 52nd Annual Grammy Awards held at the Staples Center in Los Angeles. Miley polished off her edgy look with a pair of black strappy heels from Balenciaga, Ofira and Loraine Schwartz jewelry, and a Judith Leiber box clutch. This is definitely on our list of favorite Miley Cyrus fashion moments.

13. March 7, 2010

Miley Cyrus

Miley CyrusThe Disney star went for a more sophisticated look in a dazzling full-length number by Jenny Packham, which she wore to the 82nd Annual Academy Awards (Oscars) at the Kodak Theatre in Hollywood. Miley donned a pair of diamond-and-platinum earrings from Lorraine Schwartz to finish her look.

14. March 25, 2010

Miley Cyrus and Liam HemsworthThe young Cyrus is a baby no more, stepping out with onscreen and real-life sweetheart Liam Hemsworth for the premiere of their film The Last Song, which was held at the ArcLight Hollywood Cinema in Hollywood. Miley looked absolutely stunning in an all-leather Ferragamo dress.

15. June 20, 2010

Miley CyrusIt seemed Miley wasn’t quite done with leather dresses just yet when she slipped into another one at the 2010 MuchMusic Video Awards in Toronto, Canada. The actress showed off her shorter new do along with her hot bandage dress.

16. November 21, 2010

Miley Cyrus

Miley CyrusMiley channeled a more feminine Lauren Conrad-esque look at the 2010 American Music Awards (AMAs) held at the Nokia Theatre in Los Angeles. The young star wore a dreamlike Marchesa mini dress with a lengthy train, turning to the ever-trusty Louboutins to finish off her nymph-like look.

17. February 26, 2012

Miley Cyrus

Miley Cyrus, Liam HemsworthThe former Hannah Montana actress turned to Roberto Cavalli for the 2012 Vanity Fair Oscar Party which was held at the Sunset Tower Hotel in West Hollywood. Miley brought along her most beautiful accessory to date – her hunky then-boyfriend Liam Hemsworth (sorry, we just had to).

18. May 20, 2012

Miley Cyrus

Miley CyrusA sign of things to come – Miley debuts a nose ring and side boobs at the 2012 Billboard Music Awards, which was held at the MGM Grand Garden Arena in Las Vegas. The singer wore a double-breasted dress by Jean Paul Gaultier, which she dressed up with Jacquie Aiche jewelry and a gorgeous  pair of black-and-white peep-toe Louboutins.

19. December 16, 2012

Miley Cyrus
Miley CyrusMiley transitions to her shorter blonde do at the VH1 Divas 2012 held at The Shrine Auditorium in Los Angeles. The controversial hair was paired with an Omo by Norma Kamali black turtleneck dress that had diamond cutouts running down the sides. Miley turned to her favorite Lorraine Schwartz for jewelry and opted for classic black pointed-toe pumps by Jean-Michel Cazabat.

20. February 24, 2013

Elton John Oscar Party

Elton John AIDS Foundation Oscar PartyMiley showed how an edgy short do can be worn with couture when she slipped into a white full-length Emilio Pucci for the 21st Annual Elton John AIDS Foundation’s Oscar Viewing Party. The star looked stunning in the backless embellished number, which was a refreshing breather from her leather obsession.

21. June 30, 2013

iHeartRadio Ultimate Pool PartyHannah Montana has completely disappeared in a dominatrix-like mini bondage dress by Versace, which Miley wore to the iHeartRadio Ultimate Pool Party. Miley chose suede pointed-toe pumps by Jean-Michel Cazabat to complete her not-so-poolside-party look.

22. August 9, 2013

US premiere of PARANOIA

Paranoia LA PremiereMiley returns to leather in a black, red and snakeskin patchwork leather dress by Proenza Schouler (Spring 2013 collection) for then-fiancé Liam Hemsworth’s Paranoia film premiere. Miley wore her dress with white platform heels from Saint Laurent and a Chanel Boy bag. It was the last time that the two were photographed together.

Credit: WENN/Nikki Nelson/Mike Stotts

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