The uniform dujour

[Crankin]

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.

[malkin]

My most chic urban riding kit is bike shorts under a utilikilt.

[moderncyclista]

Dude. I pretty much only see/hang with people who ride in jeans/capris/manpris. It definitely takes some fine tuning as to - jean choice/underwear choice.

I can go over 10 miles in jeans. Longer than that and I'd want some cycling shorts underneath. I agree though that Keens, jeans, hoodies is a pretty standardized uniform in urban areas.