Leighton Meester filmed scenes for the upcoming season of Gossip Girl in NYC looking superbly chic in a riding ensemble. Her character Blair covered up in a fancy olive jacket and brown leggings, then packed on the fabulous accessories: a cloche hat, an orange-and-blue printed scarf, a crocodile-print Salvatore Ferragamo bag, and black riding boots. While this look is far too covered up for Summer, it would be perfect come Fall and Winter. To start prepping for the chill, shop similar pieces below, including a similar version of Blair's Ferragamo bag. If that's too pricey, this Ann Taylor crossbody bag ($178) would work too.
Image Source: Bauer-Griffin Online