The OTHER reason he wears that

Other than a man's wife marking him with unappealing clothing, there is another reason a man wears goofy or dated apparel. If a male gets a compliment on his clothing from someone he LIKES or RESPECTS, he will wear that item or something just like it for the remainder of his life. Occasionally, the influential female may be a sister or wife, but not usually. Mothers? Never.
Could be that, when he was 14 years old, his girlfriend told him that he looked yummy in that hoodie sweatshirt. A sexy co-worker may have said that she loved men that wear red ties.
A man once told me that males remember every negative thing that a woman tells them. That simply cannot be. I think it is the opposite. In MY opinion, men are seldom the receiver of compliments so they remember every one.

Compliment the men in your lives. Just be careful what you say.