The trick to this look is contrast! The blazer and tie are formal, almost boardroom-ready. And then comes the shorts that flip that mood completely, giving the whole outfit a fun, slightly rebellious edge. Because DiLiegro is 6 feet 8 inches tall, the short shorts also drew attention to his height and long legs rather than looking silly. The striped black-and-white socks tied the sporty part of the outfit together, while the black lace-up boots kept things grounded and masculine.
