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The most daring looks Miley Cyrus has ever worn, from see-through dresses to latex leotards

July 3, 2025
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The most daring looks Miley Cyrus has ever worn, from see-through dresses to latex leotards
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Miley Cyrus waves at fans in New York City.
Miley Cyrus in New York City on June 6, 2025.

XNY/Star Max/Getty Images

No one embraces daring fashion quite like Miley Cyrus.

The 32-year-old superstar has been wearing bold outfits since the start of her entertainment career. She’s performed in latex leotards, attended awards shows in sheer gowns, and more.

Here’s a look at those outfits and some of the other daring ensembles she’s sported so far.

Miley Cyrus wore a blazer as a dress to the 2012 Billboard Music Awards.

miley cyrus 2012 BMAs
Miley Cyrus at the Billboard Music Awards in Las Vegas, Nevada, on May 20, 2012.

Jon Kopaloff/Getty Images

Her white, double-breasted blazer with a plunging neckline was designed by Jean Paul Gaultier. With this daring look, Cyrus proved she was way ahead of the “no-pants trend,” which was most popular between 2016 and 2018. 

Equally bold were her accessories and hair, which included layered necklaces, black-and-white heels, and a short, volumized lob.

About seven months later, Cyrus attended a “VH1 Divas” event wearing a long-sleeved dress covered in cutouts.

miley cyrus black dress with cutouts
Miley Cyrus at a “VH1 Divas” event in Los Angeles, California, on December 16, 2012.

Jerod Harris/Getty Images

The form-fitting dress had a high neckline, long sleeves, and a straight, calf-length skirt. The garment was especially unique thanks to diamond-shaped cutouts on each side that extended from her chest to her legs.

Cyrus completed the look with black pumps, matching nail polish, and short, spiked hair.

At the 2013 Met Gala, the musician paired an optical-illusion dress with one of her boldest hairstyles to date.

miley cyrus met gala 2013
Miley Cyrus at the “PUNK: Chaos to Couture” Met Gala in New York on May 6, 2013.

Kevin Mazur/Getty Images

Though her Marc Jacobs dress appeared to be see-through at first glance, it actually had a long-sleeved, fishnet overlay atop a nude, sleeveless piece. The outer fabric was also coated with sparkles.

To keep the emphasis on her standout dress, Cyrus opted for a classic beauty look that included black eyeliner, red lipstick, and neutral face products. Her hair, on the other hand, was styled in wispy blonde spikes that showed her brown roots.

Cyrus even found a way to wear sweatpants on the red carpet that year.

miley cyrus june 2013
Miley Cyrus at a Myspace event in Los Angeles, California, on June 12, 2013.

Jason Kempin/Getty Images

She attended a Myspace event in a black bralette-style top, leather jacket, and white pumps. Cyrus also accessorized with a black handbag, layered necklaces, vibrant lipstick, and short blonde hair that was shaved on each side. 

It was her pants, however, that stole the show. The left leg of her pants was made from denim, and the right was made from gray sweatpants. 

She then wore numerous wild outfits during the 2013 MTV Video Music Awards.

miley cyrus vmas 2013
Miley Cyrus at the MTV Video Music Awards in New York City on August 25, 2013.

Kevin Mazur/WireImage for MTV

First, she wore a strapless, fuzzy leotard designed to look like a gray mouse. Underneath was a nude, two-piece set made from latex, which she wore for her infamous performance with Robin Thicke.

She also wore white Creeper shoes from TUK Footwear, a choker necklace, and tiny space buns atop her head.

Toward the end of 2013, Cyrus wore cat-print swimwear and matching platform heels for an awards show.

miley cyrus amas 2013
Miley Cyrus at the American Music Awards in Los Angeles on November 24, 2013.

Michael Buckner/AMA2013/Getty Images

The bathing suit — which had a sleeveless crop top and high-cut bottoms — was designed by Markus Lupfer. 

Though she performed in just the two-piece set, heels, and clear accessories, Cyrus later added a white jacket backstage.

She wore dozens of unique looks during her 2014 Bangerz Tour — including this leotard made from fake money.

miley cyrus may 2014
Miley Cyrus performs in Montpellier, France, on May 23, 2014.

Erick James/Getty Images

The suit — which had long sleeves, a deep, V-shaped neckline, and a high-cut bottom — was covered in fake bills with Cyrus’ face on them.

In addition to her outfit, the musician also wore oversize gold chains, a cannabis-leaf charm, and a green choker.

She also took her daring style offstage and wore skin-baring outfits for red carpets.

miley cyrus 2014
Miley Cyrus at the amfAR LA Inspiration Gala in Hollywood on October 29, 2014.

Jordan Strauss/Invision/AP

One such look was a black Tom Ford design that showed almost her entire torso. It had see-through long sleeves made from mesh and thick black straps that strategically crisscrossed over her chest.

Cyrus completed the look with a sleek blonde bob and dark eye makeup.

The following year, Cyrus put a daring twist on red-carpet elegance for the 2015 Met Gala.

miley cyrus 2014 met gala
Miley Cyrus attends the Costume Institute Benefit Gala at the Metropolitan Museum of Art on May 4, 2015, in New York City.

Charles Sykes/Invision/AP

Her black dress, designed by Alexander Wang, had a high neckline, long sleeves, and a floor-length skirt.

It was also covered in gold studs from top to bottom and had four cutouts — two teardrop-shaped ones near the neckline, and larger, half-moon-shaped cutouts across her waist.

She then paired a strapless Moschino gown with red gloves and black boots.

miley cyrus 2015
Miley Cyrus at the amfAR Inspiration Gala in New York City on June 16, 2015.

Evan Agostini/Invision/AP

In true Moschino style, the quirky dress had a sweetheart neckline and a giant bow that extended into a train. The red, satin gown was also covered in black-and-red hearts made from sequins.

Cyrus also wore black Doc Martens boots decorated with the same heart pattern.

Months later, Cyrus hit the red carpet in a sparkling suit and white boots.

miley cyrus pink suit
Miley Cyrus at a World AIDS Day event in New York City on December 1, 2015.

Greg Allen/Invision/AP

Her sparkling pink outfit included a long-sleeved jacket cropped at the waist, straight-legged pants, and a matching belt with a silver buckle.

Cyrus’ boots, on the other hand, were white, though the stars on them were a metallic pink shade.

While campaigning for Hillary Clinton in 2016, Cyrus wore a giant bow in place of a shirt.

miley cyrus 2016
Miley Cyrus campaigns at a college dorm in Virginia on October 22, 2016.

Molly Riley/AP

The blue bow, which she wore as a bralette, had a red heart directly in the middle. She also showed her patriotic side in a red-and-white striped skirt, silver heels, and a pink feather headpiece.

And though she wasn’t photographed wearing it, Cyrus also carried a sparkling red, white, and blue top hat.

Cyrus once again showed her love for see-through clothes and heart prints in 2017.

miley cyrus 2017
Miley Cyrus at the iHeartRadio Music Festival in Las Vegas on September 23, 2017.

Sam Wasson/Stringer/Getty Images

On the red carpet, she wore a heart-print crop top underneath a sheer, calf-length jacket covered in the same print. She also wore matching lace tights that were entirely see-through over a red pair of underwear.

To complete the look, the musician wore red satin sandals, matching lipstick, and heart-shaped earrings.

In 2018, the “Midnight Sky” musician put a modern twist on old Hollywood glamour.

miley cyrus 2018
Miley Cyrus at an event held by Elton John in West Hollywood, California, on March 4, 2018.

Michael Kovac/Getty Images

She attended an event held by Elton John in an asymmetrical gown partially covered in sparkles and partially made from satin. The latter side was bright pink and resembled Marilyn Monroe’s famous gown.

The other side, however, was silver and textured. The long-sleeved gown was also unique thanks to its cutout underneath the neckline and its zig-zag pattern that split the two fabrics.

At the Met Gala that year, Cyrus looked sophisticated in a black gown with a plunging neckline.

Miley Cyrus at the Met Gala 2018
Miley Cyrus at the Met Gala 2018

Jamie McCarthy/Getty Images

The halter-style Stella McCartney design also had a mermaid-style skirt and an open back that showed off her tattoos. Cyrus paired the garment with gold necklaces and a short blonde hairstyle.

Cyrus let her shoes do the talking at the 2019 Grammy Awards.

Miley Cyrus Grammys
Miley Cyrus attends the 2019 Grammys in California on February 10, 2019.

Jordan Strauss/AP

She arrived on the red carpet in a black Mugler pantsuit, which included pants that flared at the ankles, and an oversize jacket worn without a shirt underneath.

But it was her shoes that really stood out. Cyrus wore vegan heels designed by Bradley Kenneth Eyewear and made by Mink Shoes. They were black sandals with gold-chain straps and two heels in the shapes of her initials: “M” and “C.”

She continued to wear wild accessories later that year.

miley cyrus tom ford
Miley Cyrus attends New York Fashion Week on September 9, 2019.

Jamie McCarthy/Getty Images

For a Tom Ford fashion show, Cyrus wore black satin pants, a black top with a plunging neckline, and a long velvet jacket.

The rest of her look was even bolder. She donned platform boots with sparkling heels, oversize sunglasses, and a big, fuzzy hat.

At the 2020 MTV Video Music Awards, Cyrus wore a see-through dress covered in tiny mirrors.

miley 2020 vmas
Miley Cyrus at the MTV Video Music Awards in August 2020.

Vijat Mohindra/MTV VMAs 2020/Getty Images

Her strapless gown, designed by Mugler, was worn over two black undergarments.

Cyrus also wore sheer gloves covered in black beads, strappy sandals, red lipstick, and her new signature mullet.

She wore platforms again in October 2020, but this time with a larger-than-life hat.

miley cyrus fashion
Miley Cyrus and Tish Cyrus leave a New York City hotel in October 2020.

Raymond Hall/Getty Images

While leaving a New York City hotel with her mom, Cyrus was photographed in a red calf-length coat, a white scoop-neck shirt, and wide-legged leather pants with silver zippers across each shin.

Of course, a face mask was part of her ensemble, as were oversize sunglasses, layers of necklaces, and a towering top hat with a wide brim. Cyrus also wore black, alligator-print platform boots and carried a handbag with what appears to be a cat-shaped handle.

Cyrus walked around New York City in 2021 while wearing a rock-inspired outfit.

miley snl
Miley Cyrus walks around SoHo on May 6, 2021.

Raymond Hall/Getty Images

Her DIY-looking T-shirt read “Let It Rock,” and she tucked it into a plaid miniskirt. To complete the look, Cyrus also wore velvet heels with gray bows, fishnet tights, a white garter, and messy buns.

In July 2021, Cyrus performed in Las Vegas for Independence Day while wearing a flag-themed outfit.

Miley Cyrus performs in Las Vegas, Nevada, on July 4, 2021.
Miley Cyrus performs in Las Vegas, Nevada, on July 4, 2021.

Denise Truscello/Getty Images

Her sleeveless top was made from black leather with silver sequin stars embroidered on it, while her miniskirt was covered in red-and-white sequined stripes from top to bottom.

Cyrus also wore silver jewelry, black knee-high boots with the same star pattern, and a spiked mullet.

She hit the stage again two months later in a daring blouse.

Miley Cyrus performs in Atlanta, Georgia, on September 19, 2021.
Miley Cyrus performs in Atlanta, Georgia, on September 19, 2021.

Paras Griffin/Stringer/Getty Images

While performing in Atlanta for the Music Midtown festival, Cyrus was photographed onstage wearing a halter shirt with a black collar and two shining hoops of fabric that draped across her chest.

She didn’t wear anything else under the shirt, which showed many of her tattoos.

Cyrus wore a sparkling fringe dress to a Gucci fashion show in November 2021.

Miley Cyrus and Maxx Morando at the Gucci Love Parade on November 2, 2021.
Miley Cyrus and Maxx Morando at the Gucci Love Parade on November 2, 2021.

Donato Sardella/Getty Images

Her burgundy Gucci dress was covered in a sparkling blue fringe from top to bottom. It also had a thigh-high slit up its skirt, and a yellow feather belt across her hips.

Cyrus also carried a gold purse and wore metallic sandal heels.

The musician also wore her boldest pantsuit to date that month.

Miley Cyrus attends the LACMA Art + Film Gallery in California, on November 6, 2021.
Miley Cyrus attends the LACMA Art + Film Gallery in California on November 6, 2021.

Presley Ann/Stringer/Getty Images

Designed by Gucci and Balenciaga, her cream-colored suit was covered in a vibrant, floral print and the Balenciaga logo.

Cyrus wore it with a high-neck blouse underneath, a matching purse, and an oversize emerald ring.

To kick off 2022, Cyrus hosted a New Year’s Eve party with Pete Davidson and wore a colorful, three-piece set.

Miley Cyrus in Florida for her 2021 New Year's Eve party.
Miley Cyrus in Florida for her New Year’s Eve party on December 31, 2021.

NBC/Getty Images

The outfit included a sparkling blue bralette worn underneath a short coat crafted from rainbow-colored feathers. 

She also wore bedazzled platform sandals and a miniskirt made from pink lace, purple beads, and silver sequins.

She later changed into a silver set and experienced a major wardrobe malfunction.

Miley Cyrus in Florida for her 2021 New Year's Eve party.
Miley Cyrus in Florida for her New Year’s Eve party on December 31, 2021.

NBC/Getty Images

The two-piece set had a backless halter top with rips in the front and a matching miniskirt with asymmetrical pleats.

She was performing “Party in the USA” when the top part of her outfit broke, forcing her to hold it up and quickly make her way backstage. Cyrus then threw on a red blazer and seamlessly carried out the rest of her performance.

“Everybody’s definitely looking at me now,” she then jokingly sang before adding: “I’m still in the most clothes I’ve ever worn onstage.”

Early in 2022, Cyrus performed in Colombia while wearing a cutout catsuit.

Miley Cyrus performs in Bogota, Colombia, on March 21, 2022.
Miley Cyrus performs in Bogotá, Colombia, on March 21, 2022.

Guillermo Legaria/Stringer/Getty Images

Her long-sleeved outfit was black and covered in tiny cutouts. The small circular ones extended from the garment’s neckline to its pant legs, and a giant cutout with crisscross straps sat across its bodice.

In 2023, she was photographed wearing a body-hugging corset dress.

Miley Cyrus attends the Daily Front Row's Fashion Los Angeles Awards on April 23, 2023.
Miley Cyrus attends the Daily Front Row’s Fashion Los Angeles Awards on April 23, 2023.

Stefanie Keenan/Getty Images

Her Versace dress was strapless with a sharp, plunging neckline, cone top, and leather skirt.

Cyrus wore the bold garment with pointed pumps, black leather gloves, and her hair styled in loose waves.

Cyrus couldn’t get enough of daring fashion at the 2024 Grammys.

Miley Cyrus attends the 2024 Grammy Awards in Los Angeles, California.
Miley Cyrus attends the 2024 Grammy Awards in Los Angeles, California.

Kevin Mazur/Getty Images

She first hit the red carpet in a custom ensemble designed by Maison Margiela. The golden chain-link dress was entirely see-through and intricately designed with different patterns from top to bottom.

The metallic piece also showed off her many tattoos and paired perfectly with her blown-out hairstyle.

Later that night, she changed into a brown dress with a slit that reached her waist.

Miley Cyrus attends the 2024 Grammy Awards in Los Angeles, California.
Miley Cyrus attends the 2024 Grammy Awards in Los Angeles, California.

Kevin Mazur/Getty Images

The custom Gucci gown had a thin bodice with a single strap, which barely covered her chest across one side of her body.

The revealing top design mirrored the gown’s showstopping skirt, which was slit down the side starting at her waist.

Cyrus wore the dress with pointed pumps, a feather shawl, and a leather purse.

This year, Cyrus stepped out in mesh while promoting her latest album.

Miley Cyrus signs autographs while wearing a see-through mesh gown.
Miley Cyrus in New York City on June 4, 2025.

Patricia Schlein/Star Max/Getty Images

She was visiting New York City when she was photographed wearing a black, sleeveless gown that was see-through.

Designed by Ludovic de Saint Sernin, the dress had a mermaid-style skirt, a plunging neckline, and a piece of fabric tied across the collarbone.

She then took fringe to another level.

Miley Cyrus waves at fans in New York City.
Miley Cyrus in New York City on June 6, 2025.

XNY/Star Max/Getty Images

Also in New York City, Cyrus wore a Schiaparelli couture design. It included a sleeveless, fishnet dress embellished with crystals and a fringe skirt, as well as a massive, fringe-covered coat.

She also carried a Schiaparelli purse with the brand’s signature gold anatomy charms.

The post The most daring looks Miley Cyrus has ever worn, from see-through dresses to latex leotards appeared first on Business Insider.

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