First tried these on, thought the size I ordered was 2small . I'm a 9 but own a pair of fashion boots from Clarks, in a 8.5. Used the size chart and saw the European size was 39.5. I normally wear a 39. So I ordered the 8.5. My big toe in the right shoe was a little squished. These are made with a stiff leather. The leather will stretch. Wore them and within 2hrs my toe was fine. Also the leather when I bent my foot was stiff and hurt the top of my foot. I flexed the shoe a few times and the leather was bent correctly. These have become my go to shoes! They are really retro looking and beautifully made. They get softer as you wear them. You have to work with a stiff leather . If the size is correct don't rush into sending them back. You won't regret wearing these.