Leah, singer-songwriter, 24
Before: Leah always found dresses "fun and flirty," she says. "Even when I was little, I refused to wear pants or shorts." The oversize print, however, overwhelms her, as does the long, droopy hemline.
After: Vertical stripes and front buttons on the crisp shirtdress (Tevrow + Chase, $395) add stature; the dropped waist and high-placed pockets work together to stretch out her torso. Her lower body seems sleeker, too, thanks to a skirt that doesn't "cut" her at midcalf. Heels (Valentino) are crucial for acquiring extra height and presence. Bangles, Kenneth Jay Lane.