Mary Alice Stephenson, 41, 6'
High-waisted styles, like these wide-leg pants (Charles Nolan), make a long torso look more in proportion, delivering an "instant hourglass look," says Stephenson, a stylist and fashion commentator. The top (BR Monogram) is asymmetrical, so it doesn't exaggerate her shoulders. "So many people tell tall women what not to wear. Let yourself play," says Stephenson, who started experimenting with stilettos, short skirts, and ruffles in her late 30s (before, her uniform was all dark clothes and flats). She loves these heels (Elie Tahari), though she also has a fondness for jeweled sandals.
Earrings, H.Stern; ring, Frangos Nicolas