I have a cocktail ring that I wear a lot. I'm not sure if I'd call it a cocktail ring, but I guess it kind of is. It was my grandmother's and it's special, so I try to wear it as much as I can, but it's hard to wear it without feeling showy.
I wear mine usually when I'm dressed down, so it doesn't seem like I'm trying to be pretentious. If I'm wearing simple jeans and a tee shirt, I'll put it on as a "statement" piece. I'll wear it to work and just out and about during the day...it seems a little less cliche that way. I think it also looks pretty when I'm dressed up, but with the rest of my jewelry pretty simple. A cool vintage tee and blazer and jeans would give it a cool edge too.
i have a couple that are rather enormous and costume. i don't wear them that often, and only if i'm going out at night, with an outfit that is somewhat subdued.
i have a couple. i usually wear them at night (typing does not mix well with chunky rings). when i wear them out i wear one on each finger b.c they compliment each other. or maybe it could be my weird libra fixation with balance.