<p id=”par-1_55″><a href=”https://www.cheatsheet.com/tag/oscars/”>The Oscars</a> aren’t just about <a href=”https://www.cheatsheet.com/entertainment/who-votes-for-the-oscars.html/?swcfpc=1″>honoring the best in film</a>—they’re also the biggest night in fashion. Year after year, Hollywood’s elite grace the red carpet in breathtaking gowns and bold ensembles that set the standard for Hollywood glamour. Following are the 7 most jaw-dropping <a href=”https://www.cheatsheet.com/entertainment/academy-awards-same-oscars-answer-controversial.html/?swcfpc=1″>Academy Award</a> fashion moments ever, from show-stopping couture to mind-blowing risks.</p>
<h2 class=”wp-block-heading” id=”h-lupita-nyong-o-s-cinderella-moment-2014″>Lupita Nyong’o’s Cinderella moment (2014)</h2>
<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/02/Lupita-Nyongo.webp?strip=all&quality=80″ alt=”Lupita Nyong’o wore a stunning blue Prada gown to the 2014 Academy Awards” class=”wp-image-3782888″><figcaption class=”wp-element-caption”>Lupita Nyong’o wore a stunning blue Prada gown to the 2014 Academy Awards | Axelle/Bauer-Griffin/FilmMagic</figcaption></figure>
<p id=”par-2_69″>Arriving at the 2014 Oscars in a custom Prada gown, Lupita Nyong’o cemented her status as a style icon. The flowing, powder blue dress featured a plunging neckline and delicate pleats, creating a fairytale-like effect. Nyong’o’s look was completed with a gold and diamond headband, designed by Fred Leighton. She was the epitome of elegance as she took home the Best Supporting Actress Oscar for <em>12 Years a Slave</em>.</p>
<h2 class=”wp-block-heading” id=”h-cher-s-daring-bob-mackie-creation-1986″>Cher’s daring Bob Mackie creation (1986)</h2>
<figure class=”wp-block-image size-full” id=”emb-2″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/02/don-ameche-and-cher.webp?strip=all&quality=80″ alt=”Cher stands alongside actor Don Ameche wearing an unforgettable Bob Mackie creation” class=”wp-image-3782893″><figcaption class=”wp-element-caption”>Cher stands alongside actor Don Ameche wearing an unforgettable Bob Mackie creation | Bettman/Getty Images</figcaption></figure>
<p id=”par-3_68″>In 1986, Cher turned heads with a daring Bob Mackie ensemble. The elaborate black outfit featured a sheer, beaded bra top with a matching feathered headpiece, and rhinestone fringe at the bust and down the skirt. The ensemble was complete with a matching stole, and earrings. Cher later admitted she chose the look to stand out after the Academy failed to nominate her for <em>Mask</em> that year—mission accomplished.</p>
<h2 class=”wp-block-heading” id=”h-billy-porter-s-gender-defying-gown-2019″>Billy Porter’s Gender-Defying Gown (2019)</h2>
<figure class=”wp-block-image size-full” id=”emb-3″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/02/billy-porter.webp?strip=all&quality=80″ alt=”Billy Porter wore a voluminous Christian Siriano tuxedo gown in 2019″ class=”wp-image-3782896″><figcaption class=”wp-element-caption”>Billy Porter wore a voluminous Christian Siriano tuxedo gown in 2019 | Frazer Harrison/Getty Images</figcaption></figure>
<p id=”par-4_59″>At the 2019 Oscars, Billy Porter made fashion history wearing a stunning tuxedo gown by Christian Siriano. The black velvet creation fused traditional menswear with a voluminous ballgown silhouette, challenging gender norms in Hollywood fashion. The groundbreaking look sparked conversations about inclusivity and expression, proving that the Oscars red carpet is a stage for more than just glamorous fashion.</p>
<h2 class=”wp-block-heading” id=”h-halle-berry-s-sheer-elegance-2002″>Halle Berry’s Sheer Elegance (2002)</h2>
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<p id=”par-5_60″>Halle Berry’s 2002 Elie Saab gown remains one of the most memorable Oscar dresses ever. The burgundy dress featured a sheer, embroidered bodice with delicate floral detailing, perfectly contrasting a slim-fitting, yet voluminous bottom. <a href=”https://www.youtube.com/watch?v=llgL7mGYVTI” target=”_blank” rel=”noreferrer noopener”>Berry made history</a> that night as the first Black woman to win the Oscar for Best Actress, for <em>Monster’s Ball,</em> further cementing the moment as iconic.</p>
<h2 class=”wp-block-heading” id=”h-angelina-jolie-s-leg-baring-versace-dress-2012″>Angelina Jolie’s Leg-Baring Versace Dress (2012)</h2>
<figure class=”wp-block-image size-full” id=”emb-5″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/02/angelina-jolie.webp?strip=all&quality=80″ alt=”Angelina Jolie in 2012 wearing Versace” class=”wp-image-3782903″><figcaption class=”wp-element-caption”>Angelina Jolie in 2012 wearing Versace | Frazer Harrison/Getty Images</figcaption></figure>
<p id=”par-6_84″>No other Oscars fashion caused such a stir in its simplicity. Angelina Jolie’s 2012 Atelier Versace gown was simple yet unforgettable—largely due to the way she wore it. The black velvet dress featured a dramatic thigh-high slit, which Jolie emphasized with her now-famous leg pose. The image immediately went viral on social media and the actor’s leg even inspired its own X account, which accumulated over 14,000 followers overnight. Jolie remains the gold standard of how to wear a dress on the red carpet.</p>
<h2 class=”wp-block-heading” id=”h-bjork-s-swan-dress-2001″>Björk’s Swan Dress (2001)</h2>
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<iframe loading=”lazy” title=”Bjork – I’ve Seen It All (Live at Oscar 2000)” width=”925″ height=”694″ src=”https://www.youtube.com/embed/-q1sEZo7ezw?feature=oembed” frameborder=”0″ allow=”accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share” referrerpolicy=”strict-origin-when-cross-origin” allowfullscreen></iframe>
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<p id=”par-7_61″>Björk’s 2001 swan dress by Marjan Pejoski remains one of the most unconventional Oscar outfits in history. The avant-garde look, complete with a swan head draped around her neck, left audiences divided. While some saw it as a bizarre choice, others praised it as a true work of art. Regardless, it’s one of the most talked-about Oscar outfits in Academy history.</p>
<h2 class=”wp-block-heading” id=”h-lady-gaga-s-tiffany-diamond-audrey-hepburn-homage-2019″>Lady Gaga’s Tiffany diamond, Audrey Hepburn homage (2019)</h2>
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<iframe loading=”lazy” title='”Shallow” from “A Star Is Born” wins Best Original Song | Lady Gaga | 91st Oscars (2019)’ width=”925″ height=”520″ src=”https://www.youtube.com/embed/G2lysk2YXXM?feature=oembed” frameborder=”0″ allow=”accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share” referrerpolicy=”strict-origin-when-cross-origin” allowfullscreen></iframe>
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<p id=”par-8_59″>Lady Gaga brought old Hollywood glamour to the 2019 Oscars in a black Alexander McQueen gown paired with the legendary Tiffany Yellow Diamond. The stunning 128-carat gem had not been worn publicly <a href=”https://www.cheatsheet.com/entertainment/julie-andrews-audrey-hepburn-my-fair-lady.html/?swcfpc=1″>since Audrey Hepburn</a> in <em>Breakfast at Tiffany’s</em>. Gaga followed through with her homage to Hepburn’s Holly Golightly with an elegant updo, elbow-length black gloves, and Tiffany earrings.</p>
<p id=”par-9_23″>The Oscars airs Mar. 2, 2025, at 7 p.m. ET on ABC. The live show can also be viewed on ABC.com and Hulu.</p>