I find it more comfortable to wear loose clothes while riding. For most of my shorter rides, under 15 miles, I usually wear my regular clothes with or without bike shorts underneath. Sometimes bike shorts alone, but I'll carry something to put over them if I'm planning to go in somewhere. I've even ridden in jeans which I have to make sure are loose enough in the thigh. For loose pants I have to make sure that there isn't anything that is likely to catch on/in anything. For longer rides, I like to wear my jerseys so that I can keep snacks and lip balm within an easy reach.