Photo: Lorenzo Agius

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The Fantasy: '60s Mod
Megan Babineau, 23

Megan describes her look as "edgy" and then pauses; "...meets suburban," chimes in Ken. "Your hair is definitely conservative." Though Megan peppers her wardrobe with leather jackets and motorcycle boots, her highlighted shoulder-length hair is very conventional. "I have a gutsy personality, but my appearance is pretty generic," says Megan. "I'm curious whether short hair will make me look more like myself."

Dress, Catherine Malandrino, $790; 212-929-8710. Earrings, Wouters & Hendrix, $215; Shoes, Nicholas Kirkwood, $695; 646-559-5239.