I am a size 9 - 9.5 for winter (big socks)so I ordered the 9.5M. Like previous reviewers said, the boots run pretty long. I think it is the design of the boots but I personally do not believe that "pointy" boots are flattering when you already have size 9.5 shoes, but that is my take on it! So I returned that pair and ordered the 9 W to have more room on the toe box (those boots seemed narrower than the numerous boots I have tried on). Still a least one size to big! I left it there...The boots are made of beautiful leather, soft but strong and the finishes are high quality, built to last it seems. I am disappointed that model did not work for me but I will definitely give another chance to Timberland brand.