[Photos] Her Dress At The Oscars Will Be Spoken About For Centuries

5. Hilary Swank

Hilary Swank’s 2005 appearance became an instant legendary moment, proving that a dress can be entirely business in the front and a total party in the back. The midnight-blue Guy Laroche gown featured a high neckline and long sleeves that seemed modest until she turned around to reveal a breathtakingly deep open back.

This architectural choice perfectly highlighted her toned physique, which she had famously developed for her role in Million Dollar Baby. The sheer elegance of the silk jersey fabric draped over her frame like a second skin, creating a silhouette that was both powerful and incredibly feminine. Fashion critics were quick to praise the look as a masterclass in sophisticated daring, cementing it as one of the most iconic Oscar dresses of all time. It was the ultimate “winner’s dress,” capturing the exact moment she transitioned from a talented actress to a true Hollywood icon. Even decades later, that daring plunge remains the gold standard for backless glamour on the red carpet.