I used to wear briefs not too long ago. Where I live, briefs don't have this association of beign kids underware, but it's becoming "the old man underware". Unfortunately for me, I discovered this fact when I was fooling around with a girl in her early twenties and later she said "why the fuck you use those old man underware?!"
I'm making the transition to boxer briefs and now I'm used to it, but I always feel they're more restrictive than simple briefs, which I never felt that choked my balls anyway.
But they sure looks better.