I believe he's in Queens. Which might explain the incredible faux pas of not coordinating the bag and the boots.
Personally, I'd wear almost anything. Almost.
: So many guys define themselves by their boots… and yet, there’s a world of possibilities out there. If you define boots as ‘tall and black’ this may not be the posting for you! But if you are open to different opportunities and great looks… the question for you is ‘Would YOU wear them?”