TOMS are always difficult for certain people to wear. I don't have narrow feet but I have a high discomfort tolerance when it comes to my feet in new shoes. I know that with TOMS, it normally takes them a week before my feet feel comfortable in them. Once they stretch out a bit, I can honestly wear these day and night. They're not meant for hiking, rainy weather, beaches, etc. so if you use them all the time, they will most certainly wear out quickly. I use them for running errands, shopping, walking around town, etc. and they have lasted me at least a year before needing replacement (and that was with me getting caught in the rain with them several times). I'm always a size 6 in TOMS (about half a size smaller than I am in regular shoes), so think about sizing down a half size. Try walking around in them in the house before removing the tags and if they still feel uncomfortable after 3-4 days, Amazon normally offers free returns. They shouldn't be painful but they will feel tight on the sides for a bit but they always do stretch enough if you get them in the right size.