I love layers and I love leggings in the winter. Because of my height and low waist, shirt and sweater dresses tend to look like tunics on me, and I love to pair them with leggings in the winter for work and lounge wear.
Striped button down, cashmere crew neck, Cartier tank watch: the preppie private schoolgirl in me loves this snobby, stuffy, prim and proper look. I can just see the Sebagos or Tretorns on her feet. (And the field hockey or lacrosse stick in her locker.)