I honed my becoming-an-adult style in a place where half the men wear pastel popped-collar polos, and the other half wear two pastel popped-collar polos to parody the first half. The preppy influence was hard to avoid.
These days, my style retains significant nods to country-club chic, with a dose of “no really, I’m laughing at me too.” (See headband below.) And now there's more black than back in college.
Last Saturday night’s outfit was a particularly urban-preppy case-in-point. I started with a Theory dress ($375) – fitted bodices with fuller skirts are a favorite – and added a somewhat ridiculous headband; faux jewels or big fabric flowers like the ones on this headband from J. Crew ($20) should achieve the joking-but-not-joking look nicely.
My most valued accessory to wear with this look? An attitude that says "Yes, I enjoy stomping on peanut shells in my fabulous shoes and no, I'm not too dressed up for this dive bar."