The best money I ever spent.

I don't think I've ever had a pair of shoes last more than a couple years. I had some good house slippers that lasted 4 years or so. That's the record.
 
I used to be a lot harder on shoes than I am now. I have a pair of New Balance tennis shoes that are 8 or 9 years old and still in great shape.

Still wearing my 14 year old Alpine Stars motorcycle boots and I still have a couple pair of Bostonian wingtips that are at least 25 years old.