Tommy Hilfiger

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You’d think that Tommy Hilfiger, the king of men’s fashion, would have a little better taste in clothing than this. He looks like every other typical blazer-and-jeans schmoe you’d see at the local coffee shop, only his jeans are uglier and his hair is neater. You’d never guess from looking at him that he has a net worth of over 10 gazillion dollars because he dresses like he teaches Anthropology at the local University.