Olympia Bermann

Photo: Robert Trachtenberg

1 of 24
The Perfect Layered Tee
Olympia Bermann
Senior knitwear designer, J.Crew, 30

Why it's new: Sleep and workout wear no longer, these tees are soft, slouchy (in a good way), and beg to be layered. Wear two instead of a blouse or sweater for weekend errands and weekday meetings alike.

How she wears it: Bermann, who creates supersoft, flattering pieces for J.Crew, layers a striped tee and an updated take on a sweatshirt over a pencil skirt for a look that can go straight from model fittings to dinner out. "With the right accessories, I'll wear a T-shirt anywhere," Bermann says.

Why you should try it: Because it's comfortable and eclectic, yet unexpectedly chic. "I like to dress with a sense of ease," Bermann says. "Mixing casual and fancy pieces is a very modern way of dressing."

O creative director Adam Glassman's tip: Proportion is key when layering. "With a looser top, wear a snug pencil skirt, leggings, or fitted jeans."

Striped tee, J. Crew, $40; JCrew.com. Gray Tee, J. Crew, $98; JCrew.com. Skirt, Cushnie et Ochs, $795; Shopbop.com. Tassel necklace, David Yurman; 212-724-4255. Horseshoe necklace, Lulu Frost for J.Crew, $118; JCrew.com. Pendant necklace, Lulu Frost for J. Crew, $135; JCrew.com.