When Olivia Palermo takes a stroll, it's always a stylish one. Aside from staring down her arm candy, Johannes Huebl, we're also digesting the look. This time she stepped out in a utilitarian shirt dress, one we love because of its menswear-gone-girlish vibe. It melds utility, functionality, and casual ease, and pairs best with ladylike footwear to counter the heavy pockets and structure. Try a pair of ballet flats like Olivia for now, then booties and tights later on.