Earn Your Stripes

This Thakoon Addition shift dress would look just as natural on a trend-setting girl in Thailand as a young socialite in New York. The high-low hemline is a flirty touch, and I love the multi-colored stripes and peekaboo detail as well. Such verve!

Buy it: Thakoon Striped High-Low Shift Dress ($790), Bergdorf Goodman.