Jennifer Aniston Pencil Skirt and Cream Sweater

Fitted and always on-point, Theory's classic pencil skirt is a timeless workplace essential. $215 at Bloomingdale's

Tory Burch Collins Watch, $225 at Bloomingdale's

A band collar and front cutout give Theory's sweater a sleek and chic look. On Sale now at Bloomingdale's

Stuart Weitzman Three-Band Two-Tone Sandal, $445 at Neiman Marcus