Penelope looked like a classic Parisian beauty in this white and black Chanel suit and black bowler hat when she launched the Unbreakable Kiss mistletoe installation at Madison Square Park in New York City on December 1, 2008.
She was radiant in this strapless sweetheart-neckline Yves Saint Laurent navy blue gown at VH1's 14th Annual Critic's Choice Awards on January 9, 2009, in Santa Monica, California.
Penelope was exquisite in her black velvet Alaia mermaid-style gown with a gold halter neck at the 15th Annual Screen Actors Guild Awards on January 25, 2009 in Los Angeles, California.
At Spain's Goya Cinema Awards in February, Penelope took home the Best Supporting Actress award and stunned the crowd with her custom Dior black lace gown.
The day after the Goya Cinema Awards in Spain, Penelope was perfection in a cream YSL pantsuit at the 2009 Oscar Nominees Luncheon on February 2, 2009 in Beverly Hills, California. Jet lag has never looked better!
Picking up another Best Supporting Actress award at the 24th Annual Film Independent's Spirit Awards on February 21, Penelope chose a little brown dress by Alaia with brown tights and brown Christian Louboutin platforms.
Penelope was the belle of the ball at this year's Academy Awards by winning the Best Supporting Actress Award and looking classicly elegant in a 60-year-old vintage Balmain white gown and Chopard jewels.
Penelope brought the glamour when she wore this lavender Marchesa woven and draped gown to the Broken Embraces premiere during the 62nd International Cannes Film Festival on May 19, 2009.