Proof Miley Cyrus Sets the Bar High for Oscars Transformations

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Miley Cyrus Has a Sharp Edge With Massive Brooch on Grammys 2026 Red Carpet

Miley Cyrus’ style can’t be tamed.

After all, the “Flowers” singer loves to make a fashion statement—and last year’s Oscars were no exception.

Stepping out on the red carpet at the Dolby Theater with her now-fiancé Maxx Morando, Miley stole the show in her black beaded Alexander McQueen gown with a high neckline with black lace gloves. But it was the 33-year-old’s bleached eyebrows that really caught people’s attention.

And that wasn’t the only noteworthy look that the “Party in the U.S.A.” hitmaker served that night. Later in the evening, she switched up her look for the Vanity Fair Oscars party, wearing a black, strapless Maison Margiela dress—and a new haircut.

Indeed, Miley showed up to the Wallis Annenberg Center for the Performing Arts in Beverly Hills debuting a pair of blunt micro bangs, courtesy of Bob Recine. The new ‘do was snipped one inch above her brows and styled into wedges.

The Hannah Montana alum—whose attendance at last year’s Oscars marked her first time at the awards show in 17 years—has previously been open about her style journey, comparing it to her personal transformation in Hollywood.

“‘Party in the U.S.A.’ was on an album that was designed around a collection that I had created for Walmart,” she admitted on Spotify’s Billions Club in 2024. “And now I’m the face of Gucci and Dolce & Gabbana. It really shows the evolution of my career.”

Frazer Harrison/WireImage)

A year later, Miley spoke about her relationship with fashion, noting that it “isn’t always about style; it’s more about personal expression.”

“It’s hilarious, because two people that weren’t always so minimal are now finding this new way to dress and to express themselves in this stripped-back way,” she said during a conversation with Pamela Anderson for CR Fashion Book in September 2025. “I think it’s amazing, it gives us more power to express who we are rather than letting the clothes do all the talking for us.”

“That’s been a challenge and a blessing in our careers: when you’re wearing furry hats and corsets, people take you less seriously than when you’re wearing kitten heels and trench coats,” she continued. “But you’re the same person—just with some evolution, metamorphosis, and personal growth. It’s incredible that when you present yourself with a sense of seriousness and sophistication, people really take you that way.”

MICHAEL TRAN/AFP via Getty Images

And while fans await her next return to the Oscars, Miley is certainly staying busy. After all, the actress is gearing up for the Hannah Montana 20th Anniversary Special, hitting Disney+ March 24. 

Plus, she has a wedding to plan after news of her engagement to Maxx, 27, made headlines in December.

Until those big moments, take a look back at all of Miley’s best looks through the years.

John Sciulli/Getty Images for Gucci

Rocker Chic

The pop star stepped out in a spectacularly sequined minidress and green feather jacket to attend Gucci's Osteria da Massimo Bottura. 

Kevin Mazur/Getty Images for The Recording Academy

Glitzy at the Grammys

The Grammy winner performed at the 2024 Grammys in this ultra-sparkly getup.

Steve Granitz/Getty Images

Little Black Jumpsuit

The "Flowers" singer sizzled in a plunging jumpsuit to attend Tom Ford's AW20 Show.

JC Olivera/WireImage

Round of Applause

The singer accepted her first-ever Grammy award at the 2024 ceremony in this plunging cutout dress.

Matt Winkelmeyer / Staff / GETTY IMAGES

All That Glitters

Miley proved all that glitters is gold with this completely see-through gold chainlink dress.

Chelsea Lauren/REX/Shutterstock

Bare Minimum

Miley might've worn this daring suit to the Grammy's, but it was well worth the risk! 

Jon Kopaloff/Getty Images

Super-Cute Superhero

The singer and actress saved the day in this beautiful black and silver gown at the Avengers: Endgame Premiere.

Dimitrios Kambouris/Getty Images for The Met Museum/Vogue

Green With Envy

The pop star shined in this glittery Saint Laurent ensemble at the Met Gala.

Matt Baron/REX/Shutterstock

Isn't She Pretty

While supporting her husband Liam Hemsworth at the premiere of Isn't It Romantic, the actress steps out in a red dress and Adina's Jewels 14k Safety Pin earrings.

Dimitrios Kambouris/WireImage

Back in Black

For the MTV Video Music Awards, the pop star not only gave an unforgettable performance, but also makes a statement in this Dolce & Gabbanna two-piece with Giuseppe Zanotti platform sandals.

Jordan Strauss/Invision/AP

Pop of Patchwork

The young starlet brightened up her look in a colorful Proenza Schouler leather dress for the premiere of Paranoia

Jennifer Cooper, E!

Vixen in Versace

The singer showed off her fit figure in this Versace bondage mini dress and black pumps.

Jason Merritt/Getty Images

Buckle-up in Black

The 20-year-old wore another head-turning leather look.  This time, a see-through Yves Saint Laurent blouse and a leather miniskirt. 

Frederick M. Brown/Getty Images

Comfy Cool

The New Myspace Launch Event had the star rock half jean, half sweatpants by Ashish and an Alexander Wang leather bra. She tops off the look with a plastic bomber jacket.

Stephen Lovekin/FilmMagic

Fashion Rebel

At the Met Gala's punk theme, she wowed in a nearly naked mesh dress by Marc Jacobs. 

Jason Merritt/Getty Images

Peek-A-Boo!

 The star attracted plenty of attention in this gorgeous Emilio Pucci gown with sheer overlay.

Jason Merritt/Getty Images

Chic in Checkers

At the 2013 Billboard Music Awards, Miley sported a Balmain power jumpsuit with lace embroidery.

Kirkland/PictureGroup via AP IMAGES

Goth Glamour

Cyrus rocked a beautiful Emilio Pucci dress with sheer paneling and an Edie Parker clutch at the 2012 VMAs.

DiMaio/startraksphoto.com

Power Suit

Miley wore a strapless Valentino jumpsuit with a white neckline to the Maxim Hot 100 party. To complete her look, she added sleek Saint Laurent heels.

Michael Buckner/Getty Images

Fancy at Fight Night

After a streak of bold red carpet outfits, Miley went with a bohemian look for Muhammad Ali's Fight Night in Phoenix.

Jeff Kravitz/FilmMagic

Classy in Cavalli

At the 2011 MTV VMAs, Miley opted for a bold getup in this formfitting backless Robert Cavalli gown, soft updo and blinging accessories.

Gregg DeGuire/PictureGroup via AP IMAGES

Glowing in Gabbana

The pop singer shines bright in a beachy Dolce & Gabbana gown at the 2011 Kids' Choice Awards.

John Shearer/WireImage

Animal Style

The starlet reminds us she can't be tamed in an animal-print Roberto Cavalli gown at the 2011 Grammy Awards.

Jason Merritt/Getty Images

Gala Glam

Miley turned heads in a skintight mesh dress at Clive Davis' pre-Grammy bash in Beverly Hills.

ABC/RICK ROWELL

A Leg Up!

This strapless Marchesa dress with Louboutins could be one of Miley's best red carpet looks ever.

Jeff Vespa/MC/WireImage.com

Birthday Suit

It's her party and she can wear what she wants to...and that includes a revealing leather bra top, matching pants and a studded belt.

Eric Charbonneau/Le Studio/Getty Images

Leather for Last Song

The teen star's doing her best adult impression at the Last Song L.A. premiere in a single-shoulder Thomas Wylde leather dress and matching pumps. Kids grow up so fast these days.

Jason Merritt/Getty Images

Stylish in Sequins

Miley arrives at the 2010 Oscars in a sequined Jenny Packham gown that is both glamorous and age-appropriate.

Jason Merritt/Getty Images

Mini for Miley

Miles rocks out at the 2010 Grammys in a cute denim Hervé Léger by Max Azria horizontal-stripe minidress and Balenciaga heels.

Albert Michael/startraksphoto.com

Bright & Bold

What do you wear to meet Queen Elizabeth II?! For this big moment, Miley chooses a plunging persimmon Kaufman Franco gown with wraparound leather straps.

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