Carter -- don't keep a shoe that is even a little too tight. You deserve better and with your new life dawning, you won't be able to wear them as often as you would like.
Shoes are interesting because I either see them as utilitarian or as works of art. I very much admire the works of art, but I long ago realized I can't wear them. I once bought a pair of heels (that to this day I believe are the sexiest shoes ever), yet I couldn't walk from the bedroom to the front door, on carpet, without feeling the most intense pain ever. I kept them for a long time in my closet because they really were works of art and I loved looking at them. But I doubt they were actually worn beyond the front door.
Laura -- I find shoe buying very hard. I am too embarrassed to on try lots of shoes on in the store. It has something to do with salesmen and my feet. So I order lots of pairs online. Most go back, but I can try them in the comfort of my home. Also I get a much better feel about the shoe at home then in the store. I am just too self conscious to really test them in the store. I put them on, walk a couple of steps, and try to guess how they would fit into my lifestyle based on a couple of steps.