I've looked around at several pictures and am drawn to the red checked hose- what is the history of those?
Diced hose have a long history... in fact, you'll see that they are historically what gentlemen wore with their kilts. They are EXPENSIVE, though. If he were wearing diced hose, those would be leaps and bounds more formal/fashionable than any other hose, regardless of what color his shirt is.

But obviously the jacket is going to be more important in this situation, if you have to spend money on something. Diced hose would just be the cherry on top of an already complete outfit.