LENGTH is probably your most important measurement. If you pick a cup that is too long, it will probably shift, leak and be uncomfortable. If you pick a cup that is too short, you might have a hard time reaching it for removal. Next period, reach in to feel how long your vagina is.
If you can reach the end (not necessarily your cervix) easily, it's on the short side.
If you have to reach really deep or still can't reach it, it's long.
If it's in between, aim for a medium length cup.
WIDTH is measured at the rim.
If you are young and/or new to inserting things into your vagina, you will probably want a narrow to medium width cup.
If you are older and/or have had children, a medium to wide cup will probably suit you.
Once you have an idea of length and width preferences, use the size charts to eliminate the ones you don't think will fit.
The SHAPE of the cup probably has a greater influence than rim width on how "wide" a cup feels so also compare photos of those that fall into your fitment parameters.
It's not an exact science but getting into the right ball park will increase your chances of success greatly.
Being "tight" is a function of your pelvic floor (PC) muscles. Cups sit above them. You need to relax them for insertion and removal and then you can go back to holding them as tightly as you normally do. Above them, your vaginal wall muscles become less elastic as you age and/or have children.
There are more charts by other list members available at: http://menstrual-cups.livejournal.com/ta
Melissa's side-by-side comparison photos:
http://menstrualcups.friendhood.net/f52-m
Afriska's photos and guidelines:
http://en.afriska.ch/which-one-for-you1.h