I think comfort and whether or not you need to be concerned about disturbing a partner who may be trying to sleep will be your primary criterion. Also a lot depends on whether you will be lying on your back or side, or sitting up a bit. These are very personal, So I think try before you buy is the best advice. So see if you can borrow some. Cable Co. I think has lenders. If you find IEMs comfortable, they might be the most adaptable but some people cannot tolerate them.
