My husband liked the look of the TAN version of these shoes so much that he bought them even though they were only available 1/2 size larger (at the time). He wears a size 10.5 which is an 11. Although his toe box goes almost to the top of the boot, I can see that without socks he is very roomy around the heel. So yes, there's a good chance they'll be able to sit comfortably with his prescription orthotics and big white sleeveless toe box. Still, he found the fit quite good. It has a good arc, and the material is breathable and comfortable. I personally think they look like "Dad's shoes" with a two tone color and a closure that can be buttoned instead of tied. He was warned not to carry them with me, but he loves them.