I think that boxers are a part of the urban baggy fashion. And I think there has been a reaction to the trend in our culture that embraces homosexuality. And I think that tightness is associated with homosexuality--so briefs, jocks, speedos are disparaged because they are thought to be "gay." Looseness is the opposite of gayness. Or at least that is how it is perceived. Some of us grew up when the sexual revolution hit. At that time we started to embrace our sexuality in open kinds of ways. That often meant tightness. We revealed more with tight things. (And honestly, for me, I just got used to the comfort. Our balls appreciated the support. They became used to tighter underwear and jockstraps.) As things evolved (gays became more open) this tightness became associated with gayness. And many didn't want to be associated with that. I could never wear boxers. My balls could not handle the bouncing up and down. I have a problem with soreness in my left ball, so I find any style (including most boxer briefs) that does not keep the balls in place to be very uncomfortable.