These are my first FitFlops and I love them! I wear a size 8 Medium and size 9 in athletic shoes.  I ordered the size 8 FitFlops and they fit well.  I wear thin socks and insert arch supports in all my shoes.  There is plenty of room in the toe box and the width is a little too wide, but not uncomfortable. I read other reviews that recommended to order a size down......I do not recommend ordering a size down.  The boot is designed to have a degree of movement and I think that the toe room is part of the design of the shoe.  I look long and hard to find boots with NO zippers.  Zippers can get stuck with dirt and zippers let in cold and rain. These FitFlops were exactly what I was looking for in a winter boot.  I have small ankles and medium calves.  I do not recommend these boots for someone with a very narrow foot, very large calf, large ankles or extremely high arch.  I had no trouble getting them on ....and the fit was just what I was looking for.....nice and soft and flexible around the ankle.  There is enough room for leggings.  I ordered the olive and the color is very neutral and pleasing; sort of a brown with a slight green tone.  Great price from Amazon!  So glad I found these; I have not even seen them in the department stores.