On a more serious note, I really like the outfit. Serious but relaxed. It might have added to the atmosphere to see the dog, though. (Assuming this was a dog...it could have been a cat, or a Vietnamese potbellied pig, or a naughty kid....)
This man is adorable! I can't believe I'm saying this (don't take this as encouragement, Scot) but is that a scarf he's wearing? I'd like to see a little more of it. This is just a GREAT look. Why can't you find any women in NY who are this "together"?!