Rolled up jeans, check. Waxed canvas and leather bag that weighs 100lbs, check. Fitted field jacket, check. Beard, of course. Slouchy beanie, yup. Rugged lace up chukkas, check. All he's missing is his vintage 35mm camera with leather wrist strap.
Throwing together this many separate patterns can be incredibly tricky, but the focus on vintage flair, accented by the frames and the shorts (and the car doesn't hurt), helps it all come together very nicely.