Decades ago, when Boston OMG’s would graduate from college, they would march down to the local men’s haberdashery and embark upon an often once-in-a-lifetime ritual: buying a pair of shoes. I say once-in-a-lifetime without exaggeration, for it is the “Boston Cracked Shoe Look” that many Old Money Guys are still known for. They buy a … More The Boston Cracked Shoe Look