Ashlee Simpson

Ashlee Simpson flaunts her lean gams in electric-blue tapered jeans. Layering a simple black blouse on top keeps the look from appearing too youthful. The Fendi bag adds a final, sophisticated touch.

Rag & Bone

Fall’s borrowed-from-the boys style becomes a cinch when wearing trouser-style jeans. Simply pair with a tailored vest and pull on a newsboy cap, then be prepared to walk with a debonair swagger like the models did at the Rag & Bone show.

Katie Holmes

When paired with jaunty red heels, Katie Holmes’ dark-wash tailored pants transform an average outfit—black fitted jacket and black tee—into a chic, paparazzi-ready ensemble.

Eva Mendes

Proof that fall’s jeans aren’t just for casual affairs? Eva Mendes steps out on the red carpet in the season’s essential high-waist tailored style looking cool, calm, and collected.

Marc by Marc Jacobs

When worn head-to-toe, dark denim separates make for a fashion-forward daily uniform.

Chanel

For a sleek and chic denim style like those spotted on the Chanel runway, tuck tapered jeans into flat boots. Pair with a fitted three-quarter-length jacket to perfect the long, lean look.