I'm fairly new to cycling myself. I bought a pair of riding shorts a month ago or so. I felt self-conscience at first. But as stated by many folks above, once on a few groups rides where everyone wears them, I started to feel more at ease about wearing them. If i am riding to somewhere that folks are not used to seeing riding shorts, then I still wear my running shorts over top. I suppose it takes a while to get used to wearing shorts that are so form-fitting.