I'm well-versed on celebrity legging outfits given my job, and I couldn't tell you the last time I saw a celeb wearing leggings with ankle boots ... ($3600); Miu Miu Leather Boots ($2550) If ...

Deep burgundy or rich brown leather boots can add that extra ... sleek black leggings, a stylish striped sweater, and J.Crew's lace-up ankle boots. Talk about a winning winter look.