Why do people care about what their underwear looks like? For single people, at least, most people will go throughout their day with very few people seeing what their underwear looks like, so I don't understand why people need to have a cute bra, or a cute pair of panties or boxers.
And I do it, too. I saw a pair of boxers on the Express website a little while ago, and my immediate thought was "I really want a pair of pirate boxers." They had little skull and crossbones all over them. It was awesome.