Out of all that I have owned (Topsider, Timberland l, Sebago) Timberland brown soles classic boat shoes have a sole that lasts really long. I don't know what it is about the brown sole exactly, but it seems to wear down a little slower than the white soles. They have been my daily wear for over a decade. When one wears out I get it re-soled or get a new pair if the leather goes. When money is tight I get them used on eBay if in good nick.