We've long been fans of the opposites-attract styling theory — sneakers and dresses, sporty-meets-glam, you get the idea. Rachel Bilson put our styling theory into action showing off an edgy-gone-girlie combo, juxtaposing a pair of biker boots with a femme, fit-and-flare skirt. The key to making it work is easy proportions (nothing too short or too long), and her boots exude that tough-girl vibe without bordering on the costume-y or over-the-top. To add to that kick-back vibe, Rachel chose a slouchy tank and finished with Summer-staple Ray-Bans and her luxe Chanel tote in tow. Feeling inspired? Shop our editors' picks to channel Rachel's dressed-down cool just in time for the weekend.