Proof Miley Cyrus Sets the Bar High for Oscars Transformations

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Miley Cyrus’ style can’t be tamed.

Miley Cyrus, known for her bold style, certainly didn’t disappoint at last year’s Oscars.

Miley Cyrus turned heads at the Dolby Theater, arriving with her fiancé, Maxx Morando, for the event. She wore a stunning black beaded Alexander McQueen gown with long black lace gloves, but it was her dramatically bleached eyebrows that everyone was talking about.

Miley Cyrus didn’t just wear one stunning outfit that night. She also wowed at the Vanity Fair Oscars afterparty in a black, strapless Maison Margiela dress and showed off a fresh new hairstyle.

Okay, so I was completely losing it when I saw photos of Miley arriving at the Wallis Annenberg Center! She has a new haircut, you guys! It’s these amazing, super-short, blunt bangs – seriously, they’re like, an inch above her eyebrows! And they’re shaped into these cool little wedges. Apparently, the genius behind this look is Bob Recine, and honestly, he deserves all the awards. I’m obsessed, absolutely obsessed!

Miley Cyrus, who grew up starring in Hannah Montana and attended the Oscars for the first time in 17 years last year, has often talked about how her changing style reflects her personal growth and experiences in Hollywood.

Miley Cyrus revealed that her hit song ‘Party in the U.S.A.’ was originally part of a collection she designed for Walmart. She pointed out the contrast, noting that she now works with high-fashion brands like Gucci and Dolce & Gabbana, highlighting how much her career has changed over time.

A year later, Miley discussed her approach to fashion, explaining that it’s less about following trends and more about showing who you are as an individual.

She found it funny that people who used to love more elaborate styles were now embracing a simpler, more minimalist approach to fashion. In a September 2025 conversation with Pamela Anderson for CR Fashion Book, she explained that this shift is empowering, allowing people to express their true selves instead of relying on clothes to define them.

We’ve found that how people perceive you can change dramatically based on your appearance. She explained that while costumes and playful styles might not command immediate respect, the same person, simply presenting themselves in a more professional and polished manner, is often taken much more seriously. It’s amazing how much impact presentation has, and how it reflects personal growth and evolution.

While everyone anticipates Miley Cyrus’s next appearance at the Oscars, she’s keeping a full schedule. She’s currently preparing for the Hannah Montana 20th Anniversary Special, which will be available on Disney+ starting March 24th.

On top of everything, she’s also busy planning her wedding after announcing her engagement to Maxx, 27, last December.

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

The singer arrived at Gucci’s Osteria da Massimo Bottura wearing a dazzling, short sequined dress paired with a vibrant green feather jacket.

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

The “Flowers” singer sizzled in a plunging jumpsuit to attend Tom Ford’s AW20 Show.

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

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

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

The singer and actress turned heads at the Avengers: Endgame premiere in a stunning black and silver dress.

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

Miley Cyrus accompanied her husband, Liam Hemsworth, to the premiere of Isn’t It Romantic, wearing a red dress and earrings from Adina’s Jewels – specifically, their 14k Safety Pin design.

The pop star wowed the audience at the MTV Video Music Awards with a stunning performance and a fashionable outfit: a Dolce & Gabbana two-piece set paired with Giuseppe Zanotti platform sandals.

 

The rising actress looked radiant at the premiere of Paranoia, wearing a vibrant leather dress by Proenza Schouler.

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

 

The 20-year-old once again made a striking fashion statement in leather, pairing a sheer Yves Saint Laurent top with a leather miniskirt.

 

At the New Myspace launch event, a star wore a unique outfit: half denim, half sweatpants designed by Ashish, paired with a leather bra by Alexander Wang. She completed the look with a plastic bomber jacket.

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

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

 

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

 

At the 2012 VMAs, Cyrus wore a stunning Emilio Pucci dress featuring sheer sections, paired with an Edie Parker clutch.

I absolutely loved Miley’s outfit at the Maxim party! She wore this stunning strapless Valentino jumpsuit – the white neckline was such a great touch. And those sleek Saint Laurent heels? Perfect! She really nailed the whole look.

 

Following a series of striking red carpet looks, Miley opted for a more relaxed, bohemian style at Muhammad Ali’s Fight Night event in Phoenix.

For the 2011 MTV Video Music Awards, Miley Cyrus wore a striking outfit: a tight, backless gown by Robert Cavalli, paired with an elegant updo and sparkly jewelry.

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

The young actress showed off her wild side at the 2011 Grammy Awards in a striking animal-print dress by Roberto Cavalli.

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

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

It’s her party, so she’s free to choose her own outfit—and right now, that means a daring look with a leather bra top, matching pants, and a studded belt.

The young star dressed like an adult at the premiere of The Last Song, wearing a leather dress by Thomas Wylde with one shoulder exposed and matching heels. It’s amazing how quickly kids mature!

Miley made a glamorous and mature appearance at the 2010 Oscars, wearing a sparkling, sequined gown by Jenny Packham.

Miles looked stylish at the 2010 Grammys, wearing a cute, horizontally striped denim minidress by Hervé Léger by Max Azria and Balenciaga heels.

Meeting Queen Elizabeth II is a major event, and Miley Cyrus chose a striking outfit for the occasion: a vibrant orange Kaufman Franco gown with unique leather detailing.

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2026-03-15 12:47