The trick is in breaking some of the rules in a careless, yet stylish (and clearly carefully calculated) manner, while observing the rest.
It's like Picasso or e e cummings. You can sense the history beneath the unconventionality.
In Italy (esp. the North) the Car Shoe driving shoe is possibly the most common casual footwear for well dressed men, and very seldom are they worn with driving in mind. Lapo is not the first person to wear them with a suit. His penchant for sneakers with suits, however, is a somewhat different matter....
From my experience, they gain a great look after good wear, and once completely destroyed they can easily be replaced, although they have become repulsively expensive.