I lost my original wedding ring (commitment cermony ring) just a few months ago. I've lost a bit of weight, and it was getting to the point where I needed to get it resized, but hadn't. My partner took me to the batting cages for a fun night out and I slipped it into my pocket because it was giving me problems. At the restaurant, I pulled a bunch of quarters out of my pocket and threw them in a tip jar, and the ring apparently went with them. We went back to find it but it was gone.
She got me a replacement ring (proposed again and everything - it was very sweet). It fits really well so I wear it everywhere now, even playing ice hockey. I worry about losing it again if I take it off, so the only time I take it off is at night or in the shower. It's a flat silver band with gold engravings, so I don't have to worry about it catching on anything. My fingers swell during biking and hockey, but not enough to make the ring painful.
I really don't know what I would do with a ring with jewels on it - maybe put it in one of those small plastic jewelry bags and safety pin it to the inside of my shirt. I wouldn't want to leave it in the car but I would be okay leaving it at home. Maybe put it in your bike or tool bag if you have one. I know some people who wrap their ring fingers with medical tape and then put on the gloves (both for hockey and biking). Whatever makes you feel most comfortable.
