I go commando when wearing jeans or similar type pants
I wear CK boxer-briefs with suits and khakis
I wear tighter fitting briefs with shorts as I dont want anyone looking up my pants and seeing iAlan Junior!
Hugo Boss makes some dang nice suits.. I didn't know they made underwear.
Freshpair.com has been having a sale on underwear lately (in honour of National Underwear Day, I guess... at least, they've got the banners all over the website). I have to pick some stuff up, cheap.