I always wear bike specific clothes when I ride. And SPD or SPD-SL shoes to go with the pedals. I have no bikes without clipless pedals. All of my rides now are recreational rides. No utility rides. Well I guess I sometimes ride to a store for some reason but the stores are a distance so the ride becomes a longer recreational ride anyway. Many decades ago I rode my bike to elementary, junior, and high school. I wore whatever clothes I was wearing in school that day. No helmet unfortunately. Today I only, mainly, go on recreational rides and wear bike shorts and jerseys and bike shoes and helmets. And sunglasses with a mirror.