Michael Goorjian - "Deal of a Lifetime"

Interesting thing about this scene is that early in the movie the character is seen wearing boxers. When the Devil sets out to embarrass him though, by stripping him in front of his classmates, he is in briefs. Was he just wearing briefs that day or did the Devil know that the best way to embarrass him would be by switching the boxers to briefs as part of the humiliation? Never understood why anyone would be embarrassed being seen in boxers ... they are just like being in shorts.