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It's cool if he wants to and doesn't let the haters say he can't. Maybe less cool at a job interview for a conservative law firm, than out with friends.
I think of VS Pink as strictly a juniors line, so I would say it depends on the age of the guy. Also on whether he's wearing it as fashion or in a more ironic way.
Pink is great, VS can be a little cheesy tho. You got to be careful or you’ll end up with a shoe chair under a poster of a corvette. Very few people are equal to a shoe chair and a poster of a corvette.