Gotta go with 7/Diesel/Levis Capital E. I go for mostly straight leg but I do purchase boot cut. My recent impulse buy were J Crew's straight leg selvage jean and they are actually very nice. Great fit and wash. Might have to look at J Crew again in the future.
IEMs can be extremely comfortable. You just have to find the right sleeves and the right fit. Foamies are a lot more comfortable than the rest. After prolonged listening periods, I don't even realize that I still have my E3s on.
I'd have to say that the HD280s are a good set of headphones for the price. I can't say that I'm a big fan of closed cans but they do sound pretty good for gaming. Amazon doesn't carry it right now but they used to have it on sale from time to time at ~$65-70.