Well, I think you have to wear your underwear well, because if you don’t regardless of how sexy they are, they won’t make you feel or look sexy. For example, I am not a huge fan of boxers, but on some guys they are just drop dead sexy. I love low-rise/no-show briefs, but on some guys, they just don’t look good at all. I will say this – I have yet to find a guy that looks amazingly sexy in full briefs…old school tighty whiteys isn’t a look I have seen too many people be able to carry well!
Here’s the Obviously jockstrap I got from a friend a while ago. I don’t happen to think it looks good on my from behind, but here’s both shots!