I hate to be on the Italian bandwagon, but really....when Americans do jeans and a jacket it just never (rarely) looks this cool. (Even though he is wearing mostly American brands like Ralph Lauren - or American inspired, the jeans are "Roy Rogers")
Actually, in GQ I called this look Raphael Lorenzini.
Again, this is not really about price or brand - but fit.
Those jeans are SLIM, the shirt collar high, pocket square prominent, the jacket sleeve very slim and at the perfect length, and the tie at just the right angle of sprezzatura!
I know I am not Italian, and to copy this look too completely would not feel right to me. However, I study images like this and try to figure out what element would make a difference in my wardrobe. From this image I'm reminded to ask for, or look for a jacket with a slimmer sleeve or higher armhole. That one element can make the torso of your jacket look so much slimmer.