I used wear a lot of jewelry. Now I wear my wedding band, which is a skinny gold band with a circle of diamonds and my birthstone ring (golden topaz), which my dad brought back from Japan for me when I was 13. I also wear earrings, usually a pair of larger gold studs. Oh yes, and a watch. When I am dressed for work or something more than lounging around, I usually have a bracelet on, too. Most of those I inherited from my mom; a couple were gift from my husband.
When I ride, I keep the rings on. Once in awhile, the birthstone bothers me under full fingered gloves, but then I will turn it around or adjust it and it's fine. If I want to wear a watch while riding, I have a plastic Nike watch that Trek Travel gave me for going on 2 tours with them. It has a lot of features I don't use. I never use my HR monitor anymore; I was paying more attention to it than to enjoying my ride.
I recently stopped wearing my earrings while riding; the holes where my ears are pierced are enlarged and I can't wear anything except studs with the big plastic backs. I lost the earrings Steve bought me for Mother's Day last year when I was taking my hat off at the theatre a couple of months ago. They are constantly falling out of my ears just from a slight touch, so I quit wearing them because the helmet sometimes knocks them out. I want to have surgery to fix the piercings, but insurance doesn't pay for it; I am going to save up and have it this year, hopefully.