One Outfit, Five Body Types

If You're Small Waisted but Bottom Heavy...

Try these lightweight stretch wool pants (Michael Kors, $750). They start out fitted but get fuller in the leg (so they glide over thighs) and widen out at the hem. (Not for petites, because in shortening the pants you lose that flattering trajectory.) Club Monaco's lean Kara shirt ($79), with a clean-lined vertical placket, has its own built-in scarf—nice for framing the face.

Belt, Gucci. Shoes, Charles David.