I bought these boots thinking cloth material would wrap my legs nicely. It is a bit loose though. I do have long skinny legs however. shoe size itself fits well. I'm a true size 8 and 39 fits ok. I haven't walked around in them yet but I'm confident they wouldn't hurt. It has enough room to wear with thick socks even. It does look like wearing loafers with knee high socks. Looks great with dress and pants but not sure it goes well with shorts. The only thing I don't like with these shoes is that sole feels like it's made of plastic therefore slippery on tiled surfaces so be careful specially walking around in them in malls