On casual rides I might wear some narrow-leg jeans if it's cooler. Or if it's warmer I usually wear some narrow-leg cargo pants (look like MTB shorts but no padding). I used to be all about the loose/baggy stuff but I'm way over that now as they're usually just annoying. I also have a high-vis running shirt that I sometimes wear, since I don't need jersey pockets if I have pants pockets.

Sometimes I do wear some spandex briefs under my shorts as they do a better job at moisture wicking than regular cotton boxers and the like.

For commuting I usually wear high-vis jerseys and regular bike shorts. This week I did commute a couple days with the briefs and cargo shorts, plus high-vis, and it wasn't bad.