I couldn't ever wear jeans on a ride. I can go about a mile without a chamois. That's about it.
I have built up a wardrobe of "urban cycling" stuff, that often has a detachable liner and looks nice enough to wear without the liner for anytime. Same with wicking or polyester/lycra tops that serve many functions. I wear this stuff for my errand rides and just hanging around, walking, etc.
When I commuted, it was 13.8 miles, so I wore my regular cycling clothes and rode my road bike.