Lisa needs to be comfortable in her job, but too often comfortable equals sloppy. "These flannel pants (Lands' End, $50) work because they stretch, while also giving Lisa some shape," says Adam, who finishes the look with a dressed-up T-shirt (Banana Republic, $34) and a cashmere waffle henley sweater (L.L. Bean, $119).
Earrings, Jenny Bird. Scarf, Bindya New York. Watch, Michael Kors. Bag, CC Skye. Shoes, Gap.