Image from Men's Fall Trend Report
First: Look at the wear of your shoes. You may need an update if they look like they've...been...places. As in they've been everywhere and every one can tell. I'm not sayin' throw out your bff's that have traveled far and wide and in your back yard while you were having that awesome party and...you get the picture.
Second: What era are these sole-bearers from? Shoes are one of those rare items (like watches and ties) that don't need to be turned over every season. But if the last time you bought a pair of shoes was when you started that new job...seven years ago. Let's be realistic and slip on a new pair.
Third: Are they practical for your work/social/other hobbies of your lifestyle?
Fourth: Details. Are you a black-shoe-only man? Check out toe detailing, studding (tasteful), stitching, and etc. to get the most versatility.
Fifth: Wear and enjoy.
Sixth: Repeat when necessary.
Image of Michael Bastian Gant Fall 2011 preview