During the school year, I commute 25-30 miles a day. Seldom do I wear cycling shorts. I ride Brooks saddles, and have found recently that cotton knit boxers from The Gap along with lightweight shorts are the most comfortable thing to wear. My last two rides with lyrca tights were not as comfortable. Not bad, just not as nice as with regular shorts.
I'm registered for a long charity ride - 330 miles in 4 days. If I were to ride in what my butt tells me is most comfortable, would I regret it after 40 miles or so? I've ridden up to 40 miles in regular pants, by the way, and it seemed fine.
Also, can anybody recommend a cycling short with minimal padding?