1997: Winona Ryder

During the 1990s, Winona Ryder was at the top of her game. She saw her most tremendous success up to that point, with films like Mermaids, Edward Scissorhands, and The Crucible. When the actress attended the 1997 Oscars, it was given that she was the center of attention. At the ceremony, she was accompanied by her close friend, Kevin Healy. On the occasion, she wore a black vintage beaded dress, which was complemented with her bag of the same color. Her attire was designed by the French fashion brand Chanel, which can cost you extra on your credit cards if you were to buy it.

While Ryder’s outfit today is celebrated as one of the best dresses of the 1997 Oscars, it actually received less than stellar reviews at the time. Many said that the outfit made her look like a flapper. These reviews eventually were eclipsed with more positive ones in later years.