Need to accurately depict a Sales Rep

Trying to summarize, this guy is a huge embarrassment to his father, our actual rep, and I'm guessing they chose this style of personal image for his sake alone. Huge drunk, rehab a few times, and I once witnessed him wear sandals, jorts, and a howl at the moon t-shirt to an Annual Rep dinner that is always business formal. (He was not being ironic.)

Please fark this to depict a more suitable image. Thanks in advance!