The Most Iconic Award Show Looks of All Time

7. Grace Kelly at the 1955 Academy Awards

Grace Kelly was a definite underdog at the 1955 Academy Awards. Judy Garland was the favorite to win Best Actress that year, but Kelly refused to be upstaged. She chose a look that was the picture of understated elegance, that put the focus on her beauty instead of any daring sartorial choices. In fact, she had actually worn her outfit before, to the premier of the movie that she was nominated for.

The gown was an ice-blue satin column dress, gathered down the front with just a hint of a train. She wore it with opera-length gloves. For the woman who later went on to marry royalty, it was the perfect choice.

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8. Halle Berry at the 2002 Academy Awards

Halle Berry was the undoubted star of the show at the 2002 Academy Awards. Not only did she win Best Actress for her film Monster’s Ball, she also showed up in a stunning gown, a gorgeous, sculptural skirt in red satin, paired with a net top that was almost entirely see-through except for some carefully placed flower embroidery. The gown was designed by Lebanese designer Ellie Saab, the first time anyone had worn any of her pieces on the red carpet.

9. Madonna and Michael Jackson at the 63rd Academy Awards

In 1991, the two biggest pop sensations in the world were Michael Jackson and Madonna. Both of them were at the top of the charts, but the last thing that anyone expected was for them to show up at the Academy Awards that year together.

To top it all off, they were both wearing luxuriant outfits. Madonna’s was a gown with a bejeweled bodice, and a gigantic white fur stole on top, while Jackson wore a white suit jacket studded with rhinestones, and black pants cinched with a gigantic gold belt. To say they cut an impressive figure together is an understatement.

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