Karen Lee Grybowski, 56: Instead of following fads to the letter, adapt them to your age: The jacket of this tuxedo-style suit is generously cut, while the pants are narrow (Tommy Hilfiger, $298 and $228). "I'd wear this!" says Grybowski, who loves neutral colors and silver jewelry—not to mention silver shoes (Stuart Weitzman). Layered chains (Roxanne Assoulin for Lee Angel, Gemma Redux, and Marie Chavez) look ladylike, not rock 'n' roll, with the well-bred pantsuit. The clutch (Adriana Castro) adds a touch of color. Tank, Gap, $15.
Melissa Napoleon, 26: A loose blazer gives you freedom of movement...plus, you can throw it over a glittery minidress (Madison Marcus, $548) or wear it with old jeans. Just roll and scrunch the sleeves on this sharp cutaway blazer (Elizabeth and James, $395) and you're set. "The big jacket balances the girliness of the dress," says Napoleon. "It's masculine and feminine in one outfit." Bare legs and short boots (Bruno Frisoni) look modern. Necklaces, Dannijo. Clutch, Foley + Corinna.
Maiysha, 31: "I've never been much of a suit girl, but this jacket makes me feel sexy and polished," says Maiysha. The oversize olive blazer (Ali Ro, $325), cinched with a funky multibuckle belt (Devi Kroell), emphasizes Maiysha's waist ("the smallest part of my body"). The reasonably short hemline on her sleek dress (J.Crew, $168) is perfect for 30-somethings. Tiger's eye beads, M.C.L. by Matthew Campbell Laurenza. Bag, Bottega Veneta. Watch, Tissot. Shoes, Rock & Republic.
More fashion advice: Are tunics in or out?