I usually wear padded cycling shorts on my commute, with some gym shorts over them, cuz I don't like to show off...

Today I wore my regular boxers with cargo shorts because my only pair os cycling shorts were still wet from hand washing them last night..and a little stinky too (not quite laundry day yet). I started to get some chafing towards the end of my ride this morning (13 miles)... just riding around my neighborhood I just wear the regular shorts with no problems though.

My biggest issue with wearing regular khakis or cargo shorts is that I'm in freakin HOUSTON! There is no way. They would be so soaked with sweat, they would look horrrible when i got off the bike. Much worse than anyone things bike specific shorts look. That's why i like the baggy bike shorts... they look normal but perform well for cycling.