(1 of 10) Katie HolmesKatie Holmes’s private life isn’t the only thing that’s caught our interest: From her early Dawson’s Creek days to her current place under the paparazzi spotlight, Holmes has proved herself a master at pulling off the timeless, pulled-together look. Long preferring a crisp palette of black and white for both red-carpet debuts and soccer-mom moments, she fuses effortless chic with Old Hollywood glamour. July 2000
Pairing a snakeskin skirt with a simple white tee, Holmes perfected the personalized, high-low look for the New York City premiere of X-Men.