Uptown: "W.E." Gala Screening During the Toronto International Film Festival
Look: The 53-year-old pop singer, actress and designer attends the premiere of the new romantic drama she directed and co-wrote based on the love affair between King Edward VIII and American divorcée Wallis Simpson wearing retro waves, top-lined lids, mascara and bright red lipstick.
Downtown: Vanity Fair 2011 Oscar Party
Look: Madonna parties in West Hollywood with her 14-year-old daughter Lourdes donning pin-straight strands, groomed brows and peach lips.
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