2002: Cameron Diaz

Cameron Diaz changed the tide of the game when she donned a boho dress by Ungaro Couture at the Oscars in 2002. With the style difference, this outfit was even dubbed as one of the greats in fashion history. However, to secure this dress, she made a last-minute shopping trip, thanks to her trusty credit card. She used to buy her red carpet attires from Barney, but this time was different.

At the time, Diaz admitted she had forgotten she was going to the event and did not even have a dress to wear. Thankfully, Gucci Westman called in a favor and found the floral, floor-length gown. The actress then stuck to her casual-chic style and threw her hair up into a messy pony to complete her style. She accessorized herself by wearing a chunky turquoise bracelet, which cost $20. Westman then finished the actress’ look with barely-there makeup.