I could see Superga's (or any canvas shoe) working with an un-structured cotton suit with a polo underneath, In summer but don't imagine it to ever work with a shirt and tie. Winter calls for proper lace up shoes or at the very least some chukka's if you want to casualize it. IMO of course.
No, but I'm happy for you to tell me what it means?
The number equates to you chest circumferance in inches - so if you have a 44 inch chest you should, in theory, wear a size 44 suit.
As body shape and cut of suit vary considerably, this should be taken as a rough guide only. With your proportions I would think a 44 may be too big for you, but if you go down a size, you could need some alterations in the jacket.
FWIW, Pat is someone who likes to mess with so-called convention, push the envelope a little and see what happens.
When he wants to, he can go ultra-CBD sharp. Occasionally however, he enjoys putting something out there that makes people go: What the heck??!!
It's just who he is.
Personally, having dealt with him on multiple occasions, I think he's a really nice guy with passion for his craft and an excellent sense of humour.