Sometimes that is a good thing and sometimes it is not.
When I ran into Giuseppe de Corato of Luigi Borrelli the other day I asked to take his photo and he kindly accepted. After a few shots I realized his navy blazer wasn’t buttoned. Knowing that one of the “rules” of menswear is to always have your jacket buttoned while standing, I mentioned he might want to button-up. He buttoned the jacket and I took a few more shots.
When I reviewed the shots, the ones with his jacket unbuttoned looked so much more natural and so much more like him and his style. The ones with the jacket buttoned felt forced, like a kid going to Sunday School.
I think this is a great example of how a healthy disrespect for “the rules” really works.