Michelle Obama, First Lady
“There’s so much to say about Mrs. Obama’s already-iconic style choices, but perhaps the most important thing to note is her willingness to repeat outfits,” as she has done with this purple dress, says Wagner. “And we’re not just talking once or twice -- the First Lady wears her favorite dresses four or five times over the course of several years. It shows people that the First Lady isn’t agonizing for hours each day about what to wear -- and that no one needs a new dress for each new function.”
GET-AHEAD TIP: Men wear the same suits again and again, and women can finally do the same with dresses.