Cher Horowitz
Leave Cher from Clueless off our list? As if! Seriously, how many yellow plaid costumes have you seen every year for Halloween? Alicia Silverstone’s suits, mini skirts and thick platform shoes were so iconic, that we doubt people will ever tire of dressing up as her character.
Megan Draper
Sorry, we love Betty and Joan too, but Megan Draper wins best dressed on Mad Men. Megan’s outfits screamed 60’s in all the right ways. Her mini skirts, colorful prints and perfect hairstyles made us envy both her wardrobe and nostalgic for the fashion of that decade.