I've been wearing the same shoes for the past fifteen years. Ok, it's not the same pair of shoes, but the same shoe. Black, three-hole Doc Martens with yellow stitching. I bought my first pair at the age of fifteen and I just go out and buy a new pair once I've worn my current pair into the ground. My theory is, if it ain't broken, don't fix it. I've found a type of shoe I like and I see no need to mess with a winning formula.
For years and years there were a couple of great shops on Yonge Street near Wellesley that sold my shoe at a great price. Every year or two I'd drop in and pick up a new pair. These stores, I remember one was called "IXL", are gone and it's become quite the challenge finding my black, three-hole Doc Martens with yellow stitching for a half decent price.
I've just noticed a hole developing in my current pair so I'll be resuming the hunt shortly. Queen Street, here I come!