Miley Cyrus Channels Pretty Woman in Controversial Cutout Dress — Who Wore It Better?

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She still has everyone worked up over her raunchy “We Can’t Stop” music video, but Miley Cyrus can’t help but cause controversy yet again with this pic she tweeted of her wearing the Pretty Woman dress.

The photo showed Cyrus and a friend posing in a hotel mirror with a soda on ice. It was captioned, “Pretty woman…Twerkin down the street.”

Miley Cyrus poses in a bold Tripp NYC cutout “Pretty Woman” dress paired with black ankle-strap stiletto sandals, showing off her edgy club-ready styleMiley Cyrus poses in a bold Tripp NYC cutout “Pretty Woman” dress paired with black ankle-strap stiletto sandals, showing off her edgy club-ready style (Credit: Miley Cyrus’ Twitter)

Miley’s outfit sparked conversations about age-appropriateness and the influence of celebrity fashion. While Julia Roberts’ character in Pretty Woman is a sex worker, the film is remembered more for its transformation story and iconic style moments.

Given Miley Cyrus’s bold fashion persona and public recognition, it’s unlikely anyone would confuse her homage for anything other than a nod to pop culture.

Julia Roberts Reveals the Truth Behind Her Iconic Pretty Woman Dress

Julia Roberts shared an interesting fact about her renowned dress from “Pretty Woman” during an episode of British Vogue’s Life in Looks YouTube series.

She revealed that she wore a red jacket around her waist in the film to cover what she thought was a “big butt.” The dress, a blue-and-white cutout piece by U.K. brand Hunza G, was paired with uncomfortable over-the-knee boots.

“I thought I had a big butt, and that’s why I wore that jacket like that in the movie,” Roberts said, adding that the boots were “really uncomfortable.”

Julia Roberts rocks an iconic '90s look with a white tank top, thigh-high boots, and a red jacket tied at the waist in Pretty WomanJulia Roberts rocks an iconic ’90s look with a white tank top, thigh-high boots, and a red jacket tied at the waist in Pretty Woman (Credit: Buena Vista Pictures Distribution)

Was Miley Cyrus’ Pretty Woman Dress Appropriate? Comparing Clubwear to Costume

Miley also wore the dress to a club, which was the most appropriate event and place for it. She was in Miami for the Miami Music Festival.

On the other hand, Julia Roberts wore it as part of her wardrobe in the movie. You can see a bit of the dress and a whole lot of Julia Roberts’ tiny waist in this PR photo:

Richard Gere (as Edward Lewis) and Julia Roberts (as Vivian Ward) in a PR photo for the 1990 film Pretty WomanRichard Gere (as Edward Lewis) and Julia Roberts (as Vivian Ward) in a PR photo for the 1990 film Pretty Woman

So, who do you think wore it better, Miley Cyrus or the original, Julia Roberts? Miley’s controversial dress is this Tripp NYC dress called, what else, “Pretty Woman”:

Tripp NYC "Pretty Woman" DressTripp NYC “Pretty Woman” Dress, $68

This dress is a bestseller! Tripp NYC had to restock this dress a couple of times already.

Fashion Moments Inspired by ‘Pretty Woman’ and Miley Cyrus

Explore how iconic styles from Pretty Woman and Miley Cyrus continue to influence fashion trends:

Unforgettable Movie Dresses That Changed Fashion Forever

  • Overview: Some film looks are timeless, from Julia Roberts’ thigh-high boots in Pretty Woman to Audrey Hepburn’s little black dress in Breakfast at Tiffany’s.
  • Style Impact: This roundup explores the most iconic dresses in cinematic history and how they continue influencing fashion trends today.
  • Featured Films: Includes legendary styles from Pretty Woman, Clueless, The Wizard of Oz, and more.
  • Read the full list: Unforgettable Movie Dresses That Made Fashion History

January Jones Channels ‘Pretty Woman’ at Polo Classic

  • Event: 6th Annual Veuve Clicquot Polo Classic
  • Outfit: January Jones donned a polka dot dress reminiscent of Julia Roberts’ polo match ensemble in Pretty Woman.
  • Footwear: She completed the look with MM6 Maison Margiela sandals, adding a modern twist to the classic style.
  • Read more: January Jones Wears ‘Pretty Woman’ Polka Dot Dress to Polo Classic

Camilla Belle Recreates ‘Pretty Woman’ Look with Nude Heels

Miley Cyrus’ Bold Fashion Statement at NYFW

  • Event: Rachel Zoe Fall 2013 Fashion Show
  • Outfit: Miley Cyrus turned heads in a red Rachel Zoe jumpsuit paired with a Moschino leather moto jacket.
  • Footwear: She completed the edgy look with black ankle boots, showcasing her unique style.
  • See her look: Miley Cyrus’ Fashion Statement at NYFW

Miley Cyrus’ Daring Footwear at the Grammys

These fashion moments highlight the enduring influence of Pretty Woman and Miley Cyrus on contemporary style.