I am either an 8.5 or a 9, and I ordered a 9 in these. 8.5 would have been uncomfortable. The toe box slightly pushes in on my pinkie toes - hopefully this changes as I wear them more. They are a good looking shoe, albeit not very suited for outdoor conditions. We live in a rural area with no paved roads and I can feel every rock on the bottom of my feet under these soles when I wear them. Granted, I am used to Timberlands which I wear 99% of the time and they are true work boots. Oh well, at least these are fashionable.