I think it's trial and error. I keep trying different thimbles, but seem to keep going back to the leather coin thimble that I can get at JoAnn's. It's $13, but I will pick them up when I have a coupon. The coin thimble is leather and has a little metal piece w/ dimples that is round that covers the pad of your finger. I wear it on my middles finger on my right hand (i'm right handed.)

I have been handquilting for 40 years and have dozens of thimbles scattered around my house. I prefer the brown deerskin leather ones. They have a little plastic disk under the tip that helps keep the needle from punching through the leather. I long ago taught myself to quilt with both hands. I wear the thimble on my right middle finger and another on my left thumb. I have never been able to use a metal one. For the one for my thumb I usually cut off some of the leather skirt as that gets in the way on the shorter appendage.

I, too, use a Thimblelady thimble. I started out with the plastic one to see if I would like pushing with the pad of my finger instead of the top. When I wore that one through I bought the stainless steel version. I love her thimbles and their sizing chart I found to be very accurate . I'm not as impressed with her needles but have used them and they are ok. I prefer Roxanne needles - usually #11. I also use the thimble on my middle finger and a rubber tip on my index/pointer finger. Get these at the office supply store. A small box of them will last for decades.

I have handquilted for over 30 years and I just use the metal ones with a raised edge. I have made holes in plastic ones and even a metal one!

If you can't get the hang of it (handquilting) see if you can get a lesson from someone live. That is what I had to do, although that was before the days of internet videos!