Why She Was Afraid to Try Denim on Denim "I always thought it was a major faux pas," Schick says. "Like something to wear to a hoedown."
Why She Loves It Now Cut and color are key. "The dark, tailored jacket is a nice contrast to the jeans," says Schick, founder of Morgen Schick Beauty Products. "I feel like I could wear this anywhere—to dinner, brunch, or a meeting."
A: Treat it the way you would a boyfriend blazer: over a pencil skirt or skinny jeans. And don't overthink it: A jacket that's broken in and fitted is best, but there are so many styles—collarless, blazer, cinched waist— that it's easy to find one that suits you.
Elegantly Waisted DKNY Jeans, $79, Lord & Taylor; 800-223-7440