I love winter shorts, but this is yet another style gamble that you can lose the house on. When executed properly, the look is young, playful, and a great way to get more wear out of your favorite shorts. However, when you roll the dice and lose, the stares you’re going to get on the street won’t be those of admiration. They’ll be looks of horror, possibly pity, and most likely secondhand embarrassment. You know, the same look you had when you informed the girl seated at the table next to you that she had a toilet paper tail. Oh, that was just us? Anyway, many moons ago, I put together some winter shorts guidelines that still hold true to this day. So, go ahead and hold off on stashing your short shorts for just a little while longer.
Photo Credit: Michael Stiegler