A T-shirt is a T-shirt. Spending hundreds of dollars on it doesn't elevate it. He was under-dressed, even if his casual outfit did cost more than my suit and tie. I once had another fashion victim tell me, 'This T-shirt cost twelve thousand dollars!' What difference does that make? If that's the message you want to send about yourself and your fashion sense, you should wear the price tag, or that should be the message on your T-shirt: 'Hi. This T-shirt costs more than a semester of college.' Or: 'Hi. I have money to burn. Please help me get rid of all this wealth.' And my shirt, in turn, would say, 'Great. Please write a $12,000 check to charity.