Not every dude can pull off short-shorts, but if you have the quads to make a mid-thigh look work, we suggest entering in our Orlebar Brown giveaway, round three! One winner will get this sleeked-up shorts and shirt combo just in time for drinks at the Maidstone or an outdoor dinner at, say, Morandi. How high you cuff—well, that's up to you! To score the the Hobson shirt ($260), and the Boston shorts ($250), go on over to our new NYC Facebook page!