Ranking Every Look Miley Cyrus Worn At The MTV VMAs From Least Bold To Boldest


Miley Cyrus at the MTV Video Music Awards on August 16, 2020.

Miley Cyrus at the MTV Video Music Awards on August 16, 2020.Vijat Mohindra/Getty Images

  • Miley Cyrus has become an iconic fixture at MTV’s annual Video Music Awards.

  • During performances and on the red carpet, she wears a variety of daring outfits.

  • Cyrus rocked a see-through dress, metallic suspenders, a bikini top, and more.

Miley Cyrus first attended the VMAs in 2008 and was dressed youthfully rather than boldly.

Miley Cyrus at the MTV Video Music Awards, September 7, 2008.

Miley Cyrus at the MTV Video Music Awards, September 7, 2008.John Kopaloff/Getty Images

She wore a fun black dress with sequins and gold beads. Zac Posen designed the look.

Accessorize with leather belts, gold jewellery, and short-heeled sandals.

Then, in 2011, Cyrus wore a greyish-blue long-sleeved gown to keep herself safe.

Miley Cyrus at the MTV Video Music Awards on August 28, 2011.

Miley Cyrus at the MTV Video Music Awards on August 28, 2011.John Kopaloff/PA Images/Getty Images

Designed by Roberto Cavalli, this garment is shaped in gray, black and gold velvet.

The open-back design was also interesting, but the floor-length gown was one of Cyrus’ simpler, more sophisticated looks.

She wore pink and orange outfits to perform “Younger Now” in 2017, but it wasn’t all that bold for Cyrus.

Miley Cyrus at the MTV Video Music Awards on August 27, 2017.

Miley Cyrus at the MTV Video Music Awards on August 27, 2017.Frederick M. Brown/Stringer/Getty Images

She first appeared on stage in a pink satin romper and added a poodle skirt towards the end of the performance.

Both outfits were brightly colored, but not her most memorable VMA look.

The musician’s red carpet outfit in 2013 was a little more fun, but still simple.

Miley Cyrus at the MTV Video Music Awards, August 25, 2013.

Miley Cyrus at the MTV Video Music Awards, August 25, 2013.Jamie McCarthy/Getty Images

She wore a vintage Dolce & Gabbana two-piece set that included a long-sleeve, off-the-shoulder crop top adorned with multi-colored jewels.

The high-waisted leggings were also colorfully adorned, and the platform sandals were plain black.

Her 2014 outfit was similar in style, but Cyrus opted to wear bolder materials that time.

Miley Cyrus at the MTV Video Music Awards, August 24, 2014.

Miley Cyrus at the MTV Video Music Awards, August 24, 2014.Kevin Mazur/Getty Images

Alexandre Vauthier designed her costume that year. It combines a thin leather bralette with matching high-waisted trousers made from the same material.

To keep an eye on her fashion, Cyrus only added silver sandals, skinny bracelets, and a blonde bob.

Inspired by Elvis Presley’s writings, Cyrus wore striking vintage style to the 2017 show.

Miley Cyrus at the MTV Video Music Awards on August 27, 2017.

Miley Cyrus at the MTV Video Music Awards on August 27, 2017.Jeff Kravitz/Getty Images

After her “Younger Now” performance, Cyrus changed into a blue Western-style set that included a studded jacket and high-waisted bell-bottom pants.

To add sparkle, the musicians also donned glittering belts, numerous rings, layered necklaces, and dazzling bralettes.

When Cyrus hosted the annual awards ceremony in 2015, she took to the stage wearing every color of the rainbow.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevin Winter/Getty Images

Beneath a cropped jacket made of bright fabric flowers, Cyrus wore a halter top jumpsuit.

The latter part had a deeply plunging neckline that added a bold element to her look and was covered from top to bottom in iridescent sequins.

One of her other semi-daring looks that night was a silver two-piece set with unique details.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Christopher Polk/Getty Images

The small mirrored outfit included a sleeveless crop top and high-waisted pants with sheer panels on the legs.

To complete the look, Cyrus wore metal sandals, chunky bracelets, and flower-shaped earrings.

The little black dress Cyrus wore to perform “Slide Away” in 2019 was understated, but styled with wet hair and strappy heeled sandals, it felt more daring.

Miley Cyrus at the MTV Video Music Awards on August 26, 2019.

Miley Cyrus at the MTV Video Music Awards on August 26, 2019.Jamie McCarthy/Getty Images

Cyrus paired a sleeveless mini dress with strappy sandals, layers of chunky silver jewelry, and a wet hairstyle that matched her glowing skin.

Combining bold beauty and fashion, Cyrus made an unforgettable debut in 2012.

Miley Cyrus at the MTV Video Music Awards, September 6, 2012.

Miley Cyrus at the MTV Video Music Awards, September 6, 2012.Christopher Polk/John Kopaloff/Getty Images

She wore a black Emilio Pucci gown with mesh sleeves, a deep neckline, and sheer panels across the back.

Her hair was just as bold. Cyrus wore blond strands styled skyward, like a thick Mohawk.

If you watched the 2013 VMAs, you’ll remember Cyrus’ standout leotard.

Miley Cyrus at the MTV Video Music Awards, August 25, 2013.

Miley Cyrus at the MTV Video Music Awards, August 25, 2013.Kevin Mazur/Getty Images

The clothing was made of fuzzy fabric and featured a gray rat face.The character had bloodshot eyes and posed with his tongue out, as Cyrus did throughout the show .

She wore an outfit with white platform shoes, a choker necklace, and tiny space buns in her hair.

An advocate for the LGBTQ community, Cyrus showed her pride by wearing the rainbow flag in 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.John Shearer/Getty Images

Agatha Ruiz de la Prada created a unique, boxy ensemble that Cyrus wore like a form-fitting mini dress.

The designer also created pink and red heels with hearts on each one.

One of her other daring outfits that year included an eye-shaped bra with pink feathers as eyelashes.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Jeff Kravitz/Getty Images

Her lip-shaped skirt was also bold, as were her thigh-high leather boots and orange visor.

She later switched to a pink Versace set that didn’t include a shirt.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevin Mazur/Getty Images

Instead, she wore pink low-rise pants with a suspender-style bralette and a metal version of the Versace logo covering her chest.

The outfit showed off Cyrus’ navel ring and complemented her glitter-encrusted sunglasses.

Prada was also involved in designing several of Cyrus’ 2015 looks, including a silver fringe jacket.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevin Mazur/Getty Images

Prada’s outerwear was bold, but not as striking as the metallic high-cut leotard she wore underneath.

Cyrus eventually put her hosting job on hold and took to the stage in an asymmetrical jumpsuit.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevin Winter/Getty Images

The daring outfit had sequin-covered long sleeves and sleeveless sides with an eye-shaped bikini top. There is one by one.

For accessories, Cyrus added heeled sneakers and peace-sign sunglasses.

Cyrus shocked the nation when she performed with Robin Thicke in a latex outfit in 2013.

Miley Cyrus performs at the MTV Video Music Awards on August 25, 2013.

Miley Cyrus performs at the MTV Video Music Awards on August 25, 2013.Andrew H. Walker/Getty Images

The two-piece matched her skin tone and created the illusion that she was wearing no clothes.

Cyrus stunned in 2020 when she hit the VMAs red carpet in a see-through dress covered in tiny mirrors.

miley cyrus 2020 mtv vmas

Miley Cyrus at the MTV Video Music Awards on August 30, 2020.Vijat Mohindra/Getty Images

her strapless gownDesigned by Mugler, it was worn over two black undergarments.

Cyrus also wore black beaded sheer gloves, strappy sandals, red lipstick, and her signature mullet.

Still, when it comes to Cyrus’ bold looks, her 2015 outfit is the best.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevin Winter/Getty Images

One of her outfits that night was a white Versace mini dress with round cutouts at the waist and hips.

It also had a small white pom-pom, which matched the large one in her hair.

At another point in the 2015 show, she opted for a shocking see-through dress covered in pastel dots.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Kevork Djansezian/Stringer/Getty Images

Mamadoux designed a unique piece of clothing Cyrus wore with white boots and glasses covering her eyes.

To promote her album Miley Cyrus & Her Dead Petz, the musician visited the press room in 2015 wearing a latex mini dress with an inflatable attachment.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Fraser Harrison/Getty Images

The inflatable said “Do It”, possibly a reference to her song “Dooo It!” From the 2015 album.

She wore a unique outfit with platform sandals and a pink headband in the shape of a pig’s nose and ears.

Cyrus’ most daring look, also worn in 2015, included silver suspenders instead of a shirt.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.

Miley Cyrus at the MTV Video Music Awards on August 30, 2015.Fraser Harrison/Getty Images

Versace designed a sparkling garment with dangling crystals made as a skirt, which Cyrus wore with silver high-heeled thigh-high boots.

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