Who: Caitlin Reilly
What: Anthropologie bottoms, Charles Jourdan purse, and Target sunglasses.
Where: Sunset and Sanborn for a quick cup of coffee.
Personal Style: "I tell people I dress like a 12-year-old boy."
Get this look—designers in the slideshow above include: Helmut Lang, Anthropologie, Alexander Wang, Alexander McQueen, and Chloé.