9. Ashley Benson Makes Hipster Haute
Pretty Little Liars starlet Ashley Benson perfected the casual-chic look with a plaid button down and a red beanie to match. Whether you reside in a Williamsburg studio or a small-town home, you can pull off the look with the right hat –and a vintage pair of dark-rimmed glasses, of course!
Get the look: Volcom Secret Message beanie in Rusty Red ($14.99, 6pm.com).