Hey whodini - Did you ever pick a pair of the Chukka's then? I'm a size 8.5 in Chucks and Clarks and recently purchsaed a pait of the Briar Oil Slicks in an 8D and 8.5D and the 8.5D actually worked out better so the 8D's are going back. They didn't have the wider widths available though or I imagine the 8EE's would also have worked. The 8.5D's also allow me to get away with thicker socks for the upcoming winter. I could have done it in the 8D's, but it was too umcomfortable from jump and I picturted them staying that way even after a break in period. Sorry I didn't see this before. Yup, I got my chukkas and sized a half down from my Purcells (or "usual" shoe size in most brands) and they fit perfectly.