I got over it in high school when I was a competitive swimmer (not very good, mind you, but our school team was tiny) and was running around in a speedo. I sometimes cringe at photos of myself in biking kit, because then I'm self-conscious, but when I'm actually riding I'm totally comfortable. I do keep meaning to pick up an ultralight coverup skirt just so that I could stop somewhere for a sit-down lunch on rides without looking quite as odd, but that's less about looking good and more about wearing something that's appropriate for the activity (eating in a restaurant, that is). Unfortunately, a skirt only works for women, in terms of not looking unusual. Maybe someone should start making cycling overkilts for dudes.
People are going to look at me and see a fattie on a bike no matter what I wear -- so I might as well be comfortable.