I got this hat in medium. I'm around a 7 1/4, which is actually what the hat says inside, not medium. The sizing chart says medium will fit up to a 7 3/4, but I'm kind of skeptical of that being possible considering the fairly snug fit on my head. So maybe go bigger if you're at the upper end of medium.

Mine came a little wrinkled despite pretty good packaging, and I still haven't managed to get it looking quite the way I want it. But overall it's a great looking hat, and after a few months of fairly regular use has held shape very well.