25 Unforgettable Dresses From the Past 25 Years

Click through to see stars' and editors' top picks from the past quarter-century.

"It's a flawless, timeless red-carpet moment that epitomizes elegance. Here she really is like a modern-day Grace Kelly. Pure class!" – Rosie Huntington-Whiteley, actress-model

"Her saffron-colored gown would have been striking on its own, but paired with bold red lips and that chic side chignon, she graduated from TV teen to Hollywood royalty in an instant." – Meeta Agrawa, deputy editor, EW

"I get chills just remembering [this dress]. It skimmed her shape and accentuated her gorgeous curves. She wasn't trussed in and uncomfortable—she had this ease about her." – Tim Gunn, Project Runway

"When you're as fabulous as 'Vision of Love'-era Mariah, you can rock a simple little black dress and still make heads turn." – Isabella Biedenharn, editorial assistant, EW

"I just remember falling in love with her, because she seemed like she [stayed true to] her roots, which was really important. She just looked hot. Her t--s were made for the dress!" – Rita Ora, singer

"It was simple and elegant but effortlessly demanded attention at the same time." – Lucy Hale, actress-singer

"All I remember is her leg and the slit. I'll never forget that dress." – Constance Zimmer, actress

"I love dresses that show imagination, [and] that was an absolutely genius dress. I would wear it!" – Helen Mirren, actress

"This is peak Gaga: kooky pretension that is either hilariously self-aware or hilariously self-unaware." – Darren Franich, senior writer, EW

"There was something so special about it, even though it was just black and white. It really had an impact on me." – Micaela Erlanger, stylist

"It was so chic — she looked like a princess." – Camilla Belle, actress

"This classic shape brings out Diana's personality: sexy, glamorous, confident, and fun. And the fact that she actually twirled her way down the press line? Pure magic." – Nina Terrero, correspondent, EW

"I loved this dress because it had an Old Hollywood feel but still felt very modern, sexy, and even a little edgy because of the cutouts." – Nina Dobrev, actress

"While a lot of times people go for broke at the Oscars, Winslet's simple red dress with a floral strap is the epitome of less is more." – Tim Stack, senior writer, EW

"There was something timeless and classic that she really pulled off. And I love that she chose pink, not the usual black or metallic. It's elegant and super feminine." – Lisa Berman, photography director, EW

"It looked amazing, because she wasn't dressed like everyone else. It was really clean... but there was a lot going on at the same time." – Zendaya, actress

"That cape did it for me — she looked sexy, stylish, and classic but still modern." – Ashley Madekwe, actress

"Cate [looks] timeless, confident, elegant, and strong." – Kate Bosworth, actress

"I just love that she didn't give a s---. This was just so whimsical." – Angela Lindvall, actress-model

"There's nothing I love more on a redhead than emerald green. I never get tired of that. She looks so breathtaking, and perfectly sexy but elegant and classy." – Rachel Zoe, stylist

"I still have a photo of this from my wall. It makes my heart sing." – Salvador Perez, Jr., costume designer for The Mindy Project and Pitch Perfect

"Sharon Stone wears the Gap? I wear the Gap! She proved that attitude — not money or labels — wins the red carpet every time." – Henry Goldblatt, editor, EW

"J. Lo's green Versace dress never would have existed if not for this jaw-dropping black gown." – Lynette Rice, editor at large, EW

"Britney and Justin in denim: the first thing that comes to mind [about red carpet looks] are the most ridiculous things." – Jerrika Hinton, actress

"The dress itself was very simple, but she threw everyone a curveball with the cornrows... and she had Brad Pitt on her arm, which doesn't hurt." – Chloë Sevigny, actress