ive found over years of trial and error that the better made the shoe, the better it will hold up over the years. With shoes you really get what you pay for. I work in NYC, and walk everywhere, and nothing holds up better for me that a nice pair of Edward Green oxfords. There are a lot of things to consider though (shape of foot, height of instep etc.). While I find EG sublimely comfortable, a man with a differently shaped foot might find them like vices. Just remember to polish them regularly, dont wear them 2 days in a row, and use shoe trees. I have a pair of EG's that are 9 years old, and everytime I wear them I get compliments. Another thing to consider is get yourself a few pair of great shoes, and also get a few pair of rain shoes. Rubber soled rain shoes can extend the lives of your good shoes by letting the good ones stay safe in the closet on rainy days. I love my EG's, but you can bet the ranch that im not slogging through nyc in a downpour in them.