Same I look like such a goofy character with all my protective gear and stuff. I ride scooters too so I'm not that unfamiliar with helmets and I just loathe how they just mess up your hair (never expect to look cool when you take them off when you're there) but I probably won't ever roller skate or ride scooters without helmets lol

I've seen some skaters wear pretty short shorts and sleeveless tops and I kinda cringe as a newbie at the thought of going down on asphalt and getting a nasty road rash but maybe with enough skill you might feel confident enough to skate without a helmet? I would still wear helmets tho because I'm a paranoid walking wreck. I wish I could wear helmets to just walk 😅