Who could forget the pink Ralph Lauren gown Gwyneth Paltrow wore to the 71st Annual Academy Awards on March 21, 1999? The blonde star, who was named Best Actress for her portrayal of Viola de Lesseps in Shakespeare in Love, accessorized with Harry Winston diamond jewelry valued at $160,000.
"It didn't fit her very well when she won an Oscar," Paltrow's actress mother, Blythe Danner, later told Us Weekly. "She's worn some gorgeous ones since then."
After a major misstep in 2002 (Paltrow secured a spot on perennial "Worst Academy Awards Looks of All Time" lists for wearing a gothic Alexander McQueen design), the 40-year-old actress redeemed herself on February 25, 2007. Wearing an apricot-colored Zac Posen gown, Paltrow walked the red carpet just 10 months after giving birth to her son Moses. Coldplay frontman Chris Martin's wife accessorized with Fred Leighton chandelier earrings and a diamond cuff bracelet.
On February 29, 2012, Paltrow played it safe in a modest white gown and matching cape. "This is my Jackie O moment," the Country Strong star told reporters on the red carpet. "This dress is courtesy of Tom Ford." The two-time cookbook author completed her look with Anna Hu jewelry and Jimmy choo sandals.
Tell Us: Which Oscars look do you like best on Gwyneth Paltrow?