These shoes are leather and pretty stiff at first, but it doesn't last long at all. I am a true size 8, and while I am able to wear these just fine (really, I am keeping them), I would recommend going up 1/2 size (not more IMO). They are very comfortable, but fit like a glove, and definitely will not work for wide feet. I wear them with naked feet and don't think they'd work even with no-show socks. When I first tried them on, I wasn't sure that I'd keep them. They were snug over the top of my normal width foot, and it felt like my toes were at the end, but doable. No blisters or discomfort though. After the second day wearing them, they're great. Somehow the footbed relaxes. Really comfortable footbed and padding, and much softer after only two days. I just wish that the leather was waterproof. I am already really enjoying wearing them and know that after the way they relaxed after only two days, I am confident that these will become a favorite go-to pair. Note: I ordered the "gray" color. I'd only give this color (or the pair I received) 2 stars. The color is not really in the gray family at all. It is very much a taupe (more of a tan/brown color) ... but different from the sole of the shoe, which is actually gray. Time and again I find myself a little disappointed in the color, especially since there is such a contrast between the leather and the sole. Update: While the product page color states "gray", once you add it to your cart the color/item description displays as "London Fog" ... which I would say is accurate. The color does look like the trademark London Fog taupe/tan color. Update: I purchased these in March. It is now October. I wear these shoes a lot! I reach for them constantly. They are so comfortable, and so very easy to slip on. I also find that they feel very secure on my feet, which is a great thing for certain activities. Although the leather is not waterproof, they dry quickly and don't have any stains or discoloration. I am considering purchasing another pair, but debating on another 8, or going up a half size to 8.5. I do still wish that the grey was really gray, and not tan/taupe. Upgraded my review from 4 to 5 stars. I really like these shoes. They are super comfortable and I can wear them all day with no foot pain whatsoever! They have never rubbed my foot, and never had any blisters, and they still look good. (I never wear socks) Just know going in that you should probably order a half size up. I did not order up. I am a true size 8, and these are totally fine on me (after several days of breaking in), although I'm sure an 8.5 would have been fine too. Love these shoes.