Riding around town, I'm usually in blue jeans. Sometimes I'll wear jeans for trail rides too (when it's cold out). I have a strap that I wrap around my pant leg when I'm on longer rides on my full-suspension, mountain-bike. When I forget the strap, I tuck my right pantleg into my right sock.
I've installed bash guards on two mountain-hardtails that I often ride in town. The bash guards serve to keep my pants out of the gears. On one of those bikes I've swapped out the original chainrings for two with a higher-tooth count. I made that swap to help make up for losing the third ring to the bashguard.
I do have cycling shorts, and I wear them for trail rides in warm weather. But in general, I just don't like to have to change clothes to ride the bike. When I run an errand, I want to just hop on the bike and go. I do wish manufacturers would put more creative energy into making that possible. It annoys me every time I go to the LBS and see a so-called commuter bike without a chainguard.