Per the advice of other reviewers, I got a half size up (I'm normally a size 10 in pretty much all of my shoes, and ordered a size 10.5 in these). I'm glad I did, because although they aren't "tight", the toe area for the big toe is not as roomy as other shoes due to its funky shape. These fit just right, and are loose enough to be a great driving shoe as well as walking around town. I'll probably get some inserts because I have plantar fasciitis and so I often do put supports in most of my shoes, but honestly the bottoms are so cushiony I might not actually need it. Super comfy, and very quirky looking. I can see where you'd either love or hate the look of them, but I like quirky things that don't make me look like a cookie-cutter version of everyone else. I'm planning to buy more in other colors.