From Classic Chic to Boldly Bizarre: Ranking the Most Unforgettable 2025 Oscar Party Looks

The 2025 Oscars weren’t just about honoring cinematic brilliance—it was also a night of fashion that had everyone talking. From understated elegance to avant-garde risk-taking, Hollywood’s biggest stars used the red carpet and after-parties as their personal runways.

This year, some celebrities embraced timeless sophistication, while others pushed boundaries with daring, unconventional ensembles. Whether they stunned with classic beauty or made jaws drop with unexpected designs, these stars left an unforgettable mark on the night’s fashion scene.

20. Kaia Gerber – Minimalist Grace

Kaia Gerber proved that less is more. Her minimalist, figure-flattering gown exuded classic Hollywood charm, with a sleek silhouette and subtle detailing that enhanced her natural beauty. She reminded everyone that elegance doesn’t need to be loud to make an impact.

Video:

Top 10 Best Looks at the 2025 Oscars

19. Miley Cyrus – Rock Glam Revival

Miley Cyrus brought rock-and-roll energy to the red carpet, blending edgy sophistication with old-school Hollywood glamour. Her shimmering ensemble, bold accessories, and confident attitude made for a powerful yet polished statement.

18. Da’Vine Joy Randolph – Regal Elegance

Fresh off her awards-season success, Da’Vine Joy Randolph exuded royalty and grace. With structured draping and a deep, luxurious hue, her look radiated confidence and poise, making her one of the night’s most beautifully styled stars.

17. Kim Kardashian – Curve-Hugging Chic

Kim Kardashian stayed true to her signature sculpted aesthetic, opting for a form-fitting, high-fashion gown that accentuated her silhouette. With sleek hair and perfectly coordinated accessories, she once again dominated the red carpet with her refined yet sultry look.

16. Demi Moore – Timeless Beauty

Demi Moore’s classic Hollywood-inspired look was a testament to effortless beauty. The luxurious fabric and elegant details enhanced her ageless appeal, proving that sophistication never goes out of style.

15. Margaret Qualley – Vintage Meets Modern

Margaret Qualley’s gown seamlessly fused old-world charm with a contemporary edge. Intricate lacework, soft draping, and an ethereal silhouette created a romantic yet modern aesthetic that stood out beautifully.

Video:

The Most Bizarre Vanity Fair Oscar Party Looks of 2025

14. Paris Jackson – Bohemian Luxe

Paris Jackson’s free-spirited style took center stage with a flowing, boho-chic look that balanced effortless cool with high-fashion drama. The unique detailing and textured layers added to her distinctive, artistic flair.

13. Hailey Bieber – Sleek and Chic

Hailey Bieber once again perfected minimalist luxury. Her ensemble featured clean lines, impeccable tailoring, and an aura of effortless sophistication, proving that sometimes, simplicity makes the biggest impact.

12. Lindsay Lohan – Classic with a Twist

Lindsay Lohan made a radiant return to the Oscars scene with a gown that blended timeless elegance with modern appeal. The sophisticated design and bold color choice ensured she made a memorable fashion statement.

11. Camila Cabello – Romantic Glamour

Camila Cabello’s look captured the essence of soft femininity and ethereal beauty. The delicate textures and flowy silhouette gave her an enchanting presence, making her a standout among the night’s best-dressed.

10. Cynthia Erivo – Avant-Garde Excellence

Cynthia Erivo is known for her fearless approach to fashion, and she did not disappoint. Her high-concept gown played with volume, unexpected textures, and artistic detailing, cementing her place as one of the most daring style icons of the night.

9. Sarah Paulson – Edgy and Empowered

Sarah Paulson went for bold and androgynous fashion, opting for a structured silhouette that combined high fashion with a rebellious edge. The sharp tailoring and striking color palette made her one of the night’s most empowered fashion statements.

8. Natasha Lyonne – Quirky and Couture

Natasha Lyonne’s eclectic style took center stage with a look that was part couture, part avant-garde, and entirely unique. With dramatic details and unconventional styling, she reminded everyone why fashion is meant to be fun and expressive.

7. Heidi Klum – Glamorous Risk-Taker

Heidi Klum has never shied away from taking fashion risks, and this year’s Oscars after-party was no exception. With bold embellishments and daring design elements, she commanded attention with her fearless fashion sense.

6. Jenna Ortega – Dark Romance

Jenna Ortega continued to refine her gothic-chic aesthetic, blending mystery with elegance. The structured yet flowing design of her gown created a dramatic and moody effect, making her one of the most striking figures of the night.

5. Julia Garner – Futuristic Elegance

Julia Garner’s look embraced high-fashion futurism, with a sculpted, almost architectural design that turned heads. The avant-garde elements made her outfit a conversation starter and a standout moment of the night.

4. Sofía Vergara – Sultry Sophistication

Sofía Vergara radiated confidence in a gown that celebrated her signature curvaceous silhouette. The intricate beadwork and impeccable fit highlighted her timeless beauty, making her one of the night’s most unforgettable presences.

3. Lisa – K-Pop Star Turned Fashion Icon

Lisa from Blackpink brought her K-pop glam and high-fashion influence to the Oscars party, delivering a look that was both boundary-pushing and effortlessly chic. Her presence on the red carpet signified the growing impact of global fashion trends in Hollywood.

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Lisa with Jessica Alba at the Vanity Fair 2025 Oscar Party

2. Doja Cat – High Fashion Fantasy

Doja Cat blurred the line between fashion and art, creating one of the night’s most theatrical moments. Her avant-garde ensemble combined fantasy, creativity, and couture, solidifying her reputation as a fearless fashion innovator.

1. Julia Fox – The Ultimate Risk-Taker

Topping the list, Julia Fox delivered the boldest, most unconventional fashion choice of the night. Never afraid to push boundaries, her ensemble was as shocking as it was memorable, proving yet again that she is Hollywood’s most daring style icon.

Final Thoughts: The 2025 Oscars Fashion Recap

From classic elegance to extreme avant-garde, the 2025 Oscars after-parties showcased the full spectrum of Hollywood fashion. Some stars played it safe with timeless sophistication, while others turned the red carpet into their personal runway for bold experimentation.

Whether embracing understated chic or theatrical couture, these celebrities reminded us why the Oscars remain one of the most anticipated nights in both film and fashion.

Who stole the show for you? The debate over the best-dressed will continue, but one thing is for sure—Hollywood’s love affair with fashion is stronger than ever.

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