Yes, it may seem rather silly to wear shorts in winter, yet it's so brilliant! I think it's especially funny since I don't particularly like wearing shorts in summer, yet there is something about layering the shorts over tights and wearing them with boots that make the seem more modest and less beach-bound teenybopper. But to do this trend right, you can't just simply throw on your lightweight summer shorts over tights and expect it to work. Choose a winter weight fabric that's appropriate for the season like wool or tweed for day or silk, leather or sequins for night. The one pair of shorts that can make the cross over? denim cut offs. They have a great rock and roll Erin Wasson feel when layered with legwear and cozy sweaters. Once you have your shorts picked out pick out a base layer like opaque tights, or get try some of this season's patterned or embellished tights for a little something extra. On top, the more layering the better, and definitely play with proportions. A micro mini short looks great with a looser sweater or top while a more fitted knee length trouser short needs something a little more fitted like a sharp little jacket or coat (extra style points for a blazer with strong shoulders). Check out the slideshow to see some of our top picks that will show off your legs even when temperatures drop.