I go with the philosphy of wear what makes you comfortable. I tend to lean towards the more traditional when in formal/semiformal attire i.e. Ghillie Brogues, but I know a lot of folks on this site have issues with Ghillies. For my more casual look I go with Sketchers or Doc Martins for the look and the comfort. Check out my gallery, I have picture of the shoes I wear when in casual attire.

As Popeye stated "I am who I am..."