Like Proctor, executive search consultant Samantha Carey, 38, struggles to find clothes that work with her upper body. "I used to buy jackets and have them taken in four sizes at the midsection," Carey says of her days as a competitive swimmer. This silk jersey dress skims Carey's shoulders while emphasizing her waist. "I've always felt unsure about what to wear outside the office or gym," says Carey. "This is a perfect solution."
Dress, Aidan Mattox, $255, edressme.com. Earrings, Irene Neuwirth, $7,770, ylang23.com. Bangles, BaubleBar, starting at $36 each, baublebar.com.