5. Leighton Meester Goes City Slicker Chic
Leighton Meester skipped a glittering headband in favor of an artsy raspberry beret for a Gossip Girl scene back in 2012. And as per usual, we’re jealous of her Upper East Side flair. Save this quirky topper for chilly spring nights. Wear with your favorite black trench, swipe on an extra layer of mascara, and feel like a Big Apple princess with a hefty trust fund.
Get the look: Unisex wool beret in Raspberry ($24, americanapparel.net).