I believe that shoes are our most important wardrobe investment. We are judged by our footwear, so spending a bit of money and some time on considering the right options will serve you well.

Here, we've compiled five of our favorite examples of these classics, accompanied by Gunn's suggestions. Get a version of these in your closet and you'll be set for life.  

Tim Gunn is a fashion expert and consultant. Follow him on Twitter.