Melissa Napoleon, 26: A fitted jacket (Express, $128)—slightly shaped, and touched with silver on lapels, pockets, and cuffs—shows that metallic trim can play as elegant or edgy. For clubbing or shopping, Napoleon wears it with a tank (C&C California, $68), black leather leggings (Vince, $895), and studded accessories (cuff, Samantha Wills; bag, Diane von Furstenberg; boots, Manolo Blahnik). The multistrand, mixed-media chain necklace (Notify) is one of fall's most popular trends.
Leigh Carlson, 56: A semitough trend like studs is tricky to pull off in your 50s, but this same Express jacket is beautifully tailored, not too severe (Carlson, an actress, likes its classic, unboxy cut). All three accompanying pieces—sweater (Martin + Osa, $70), knit pencil skirt (Talbots, $139), and leather boots (Pedro Garcia) are the same rich teal blue (a monochromatic strategy that guarantees a long, lean line). A dramatic scarf (Me & Kashmiere) puts flattering color next to her face. Tights, Wolford.
Yangchen Lhamo, 34: Many of this season's best ideas are reinventions of '80s favorites. Take the jumpsuit: This cropped-leg, high-waisted version (French Connection, $215) has a minimalist chic that makes the jacket feel more subdued. Lhamo, a nanny who plans to study nursing, is originally from Tibet. With her all-black accessories—glossy belt (Hobo International), jeweled bag (Marc Jacobs), and open-toe ankle boots (BCBG Max Azria)—she looks like a true New Yorker. Hoops, Lana Jewelry.