I wear shorts with tights over them and so does my BF. I asked him once why so many guys do it the other way. He said he didn't know of any guys that did that and thought it would be quite uncomfortable. So, I pointed out a guy that looked like he was wearing tights with shorts over them. He replied, those are leg warmers. Around here at least, where it doesn't get too cold, the shorts + leg warmers combo is pretty common for the guys.
2004 Colnago Chic - WTB Deva
2008 Blue RC7 - WTB Deva
2009 Colnago Master X-lite - WTB Deva