In New York, I feel comfortable leaving the house in anything my little heart desires. In Missouri, I feel a little too shy to throw on a dress when everyone else is in sweats or to wear fancy high-waisted skirts with my prettiest heels when everyone else is in jeans and flip flops. I've always had a fear of overdressing, and living in the Midwest
—where it's far easier to fit in than to stand out—only increases this self-conscious tendency.How do you deal with wearing exactly what you want and, inevitably, drawing a few "What is she wearing?!" glares?