In my not-so-past life as a fashion magazine addict (let’s be real—I bought seven of last month’s fashion mags for a quarter each at a recent library sale), this time of year was crucial to me. What kinds of skirts would appear on the pages of Seventeen? Would I be able to afford them? Would one-piece swimsuits finally be cool? Was this the year I started blow-drying my hair?! Each issue was a mini-New Year’s. Anything was possible.

These days, I love fashion for its feminist and political sensibilities, and I am far more into comfort than trends. I work at a job where I push the style envelope, but hey, no one said anything to me when I wore combat boots every day this winter. (That doesn’t mean I’m going to start wearing shorts to the office, though, much as I crave a temperature-sensitive dapper aesthetic. Even I have my limits.) But style? Style has no limits. Wear socks with sandals. Dress as a different character every day. Admire your reflection in the subway windows. Here are five stories about our connection with the clothes we wear.