There are many reasons to steer clear of hats from ill-fitting toppers to the threat of hat hair, but Gwen Stefani and Elizabeth Olsen prove that the right hat can add instant street cred to your everyday ensembles. Gwen paired a plaid newsboy cap with silver Vivienne Westwood jeans and peep-toe Maison Martin Margiela booties while heading into a music studio in Santa Monica, while Elizabeth chose a dark fur coat, oversized Chloe bag, and velour fedora for strolling the streets of Tribeca. Check out our picks of dapper toppers inspired by the duo; whichever style you choose, it will be sure to turn heads.

Image Sources: FameFlynet and Film Magic