The 2025 Tony Awards are coming up fast—and while the focus is always on stage talent, the red carpet deserves just as much applause. Over the past two decades, we’ve seen actors, singers, and even unexpected guests turn up in unforgettable looks. Whether it was a custom gown, a bold risk, or a surprise appearance that made headlines, these are the 10 outfits that still stand out years later.
1. Deborah Yates, 2000
Embed from Getty ImagesThe Contact nominee arrived in a silver iridescent dress that reflected the early-2000s obsession with shine. Paired with hoop earrings and a sleek updo, it felt futuristic and fully on-trend for the time.
2. Gwyneth Paltrow, 2001
Embed from Getty ImagesGwyneth attended to support her mom, Blythe Danner, but her look turned just as many heads. She wore a gold knee-length dress with a deep neckline that leaned vintage-inspired but stayed minimal and modern.
3. Sarah Jessica Parker, 2003
Embed from Getty ImagesWearing a sheer black dress by Gucci from Tom Ford’s era, Parker gave the event a fashion-forward moment. The midi dress had subtle paneling and a bold edge that aligned with her rising fashion icon status.
4. Julia Stiles, 2005
Embed from Getty ImagesKnown more for film at the time, Julia brought serious red carpet presence in a deep red gown with a plunging neckline. The dress was classic but sharp, proving she could hold her own at a major theater event.
5. Laura Linney, 2008
Embed from Getty ImagesIn a soft blush pleated gown with ruffled trim, Laura Linney kept it romantic and refined. The asymmetric hem and floral waist detail gave it subtle texture, and the whole look was peak 2000s red carpet sophistication.
6. Catherine Zeta-Jones, 2010
Embed from Getty ImagesShe wore a strapless pale blue Atelier Versace gown while attending as a nominee—and eventual winner. The soft chiffon layers and simple styling made it a standout for how polished and camera-ready it looked.
7. Kendall Jenner, 2015
Embed from Getty ImagesA surprise guest, Kendall wore a peach sequin mini dress by Calvin Klein Collection with an open back. It was clean, modern, and brought a fresh contrast to the mostly formal crowd.
8. Lupita Nyong’o, 2016
Embed from Getty ImagesLupita wore a custom Jason Wu gown covered in layered sequins, with colors inspired by geometric patterns. It was structured, colorful, and different from anything else that night—earning her near-universal praise.
9. Cynthia Erivo, 2019
Embed from Getty ImagesCynthia arrived in a voluminous custom Chris Gelinas gown with bold yellow pleats and a sculptural silhouette. Paired with a short platinum cut and minimal accessories, it was high-fashion drama with no distractions.
10. Angelina Jolie, 2024
Embed from Getty ImagesAngelina walked the carpet in a custom seafoam green velvet gown by Atelier Versace with a matching shawl-style shrug. The look went viral instantly for its statuesque fit, old-Hollywood styling, and her unexpected appearance at the awards.
These 10 outfits aren’t just pretty pictures—they each defined a red carpet moment, made a cultural impact, or set a new standard. With 2025 around the corner, let’s see who makes the next list.
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