You can buy cycling shorts that look like regular hiking shorts but have an inner liner. No way I would ride 15 miles or 30 miles wearing regular shorts and underwear. "Spandex" cycling gear may look goofy to you, but you would probably quickly get over your consternation if you actually tried them. Cycling shorts have pads that make them more comfortable for sitting on a saddle and are made of fabrics that quickly dry after getting sweaty.