I'm always on the lookout for grey flats and so I had to try these Timberlands. I ordered both the size 5.5 and 6 because I go to either size depending on brands. Sadly, I found these shoes to be really uncomfortable in the toe bed.  They put a lot of pressure on my big toes.  Doesn't  feel to me like this will stretch out or be at all forgiving.  The size 5.5 fit me well and the shoes are so cute with the brown detailed ties. The footbed is well-cushioned and they have a decent arch support for this style. Im so disappointed as i fell in love with these at first sight!  Guess i will be staying with the Born, Clark and Keen brands I love.