Simply put, short shorts or hot pants are marketed to teenagers, not you. If you've got a killer body and a youthful appearance and want to take a fashion risk, however, be sure to balance short (but never cheeky!) shorts with a longer sleeve or billowy blouse, says Dabney. "The important thing to keep in mind when pairing a top with your shorts is proportion. Save the sexy tanks for the longer mid-thigh, knee length, or Bermuda shorts," she says.