Slipping these sleek, sexy ankle booties on is not a decision made lightly. In fact, says Carol Davidson, president of StyleWorks of Union Square, a New York City-based image consultancy, “These boots say sexy, edgy and bold, mixed with a bit of 'rocker girl' chic.”

Work them to the max by pairing them with skinny pants and a one-shoulder top. A cuff bracelet completes the look. If you plan to wear them with skirts, fun up each ensemble with patterned tights.

Pictured: Brian Atwood Miri Leather Ankle Boots ($785 at Net-A-Porter.com)