I'm not a city folk but I found that tucking the inner side of my jeans into my boots saved wear and tear on my jeans from stirrups... When I was biking I never did bother to tuck as there wasnt much "friction" to ruin my jeans...Those that do tuck for bike riding need to fix the leak thats causing the oil to splatter on thier britches :)~ All in all its a matter of tastes..."booties" became popular for women there for a bit because we rarelly tuck and fashion kinda dictated that women should wear tight fitting clothes which are a pain in the butt to fit over standard boots