Karen Lee Grybowski, 56: A designer-inspired tweed jacket and ruffled silk blouse (J.Crew, $325 and $88) are nicely pulled-together...a must at 50-plus. With a coordinated skirt, they might seem too prim (overmatching can be a trap). But teamed with relaxed, rolled up jeans (New York & Company, $40), they're just right. The pants' proportions are complemented by ballerina flats (Hayden-Harnett)—"I like to walk, so I need comfort," says Grybowski, a yoga instructor and model scout. Earrings, Nava Zahavi. Bangles, Yossi Harari. Belt, Kristin Kahle.
Kelley Lauren Hicks, 24: Boyfriend jeans save money—whether you "borrow" from a guy, buy them secondhand, or find a bargain like this Old Navy pair ($35). "These are cute and roomy," says Hicks, who isn't a fan of tight pants. Pulling them in with a belt (Belgo Lux) keeps the fullness under control, and there's a dashing street-fashion feeling to the Sgt. Pepper–style military jacket (Alice + Olivia, $550), messenger bag (Treesje), and multistrapped shoes (Bottega Veneta). Tank, American Apparel, $17.
Maiysha, 31: "My generation is lucky," says this singer-songwriter (Grammy nominated for her single "Wanna Be"). "Those Sex and the City women showed that turning 30 is no big whoop." Jeans (J Brand, $275) and a dressy sweatshirt (Elizabeth and James, $465) combine comfort and glamour. The cuffed jeans look best rolled to above the ankle, where the calf is narrowest; boots (Brian Atwood) will fill the gap. Earrings, Kimberly McDonald. Bracelet, Badgley Mischka. Bag, Chanel.