Some guys shop with patience of Job, waiting months and diligently scouring sale sections for just the right deal. On the other hand, there are those guys that regularly pour out a small fortune just to look like they found their clothes in a dumpster. Most of us probably fall somewhere in between, splurging and scrimping from time to time. And then, there’s Diego Della Valle, a man that simply dresses like pure opulence. Of course, it helps that Della Valle is the CEO of a little company called Tod’s footwear so he pretty much dresses up to his title, but when it comes to Della Valle, as with so many other Italian icons (a pack lead that’s lead by Gianni Agnelli who helped elevate Tod’s to another level when he wore them back in the day) how you wear it is often far more important than what you wear. In fact, Della Valle’s clothes themselves are not particularly remarkable (although he is a great template for proper fit, particularly for bigger guys) mainly focusing on blue shirts, navy or grey jackets, washed denim and of course Tod’s.