I actually saw a fit very similar to the picture in the OP on the subway yesterday. This young dude, maybe 21-24 had a very nice fitted trenchcoat. From his grooming, it seems like he may be metro (tweezed eyebrows, etc). Plus he had good layering going on, letting 1/4" of his sweater show outside the sleeve of his trenchcoat. Everything fitted great. Then I saw the boot tuck.... my gut reaction was that it was WRONG, although everything fitted the guy well, everything looked so "forced" as someone had say. Though I was indifferent before, I now would put the boot tuck in the same category as the half-tucked shirt, or the flipping up of jacket/blazer collars indoors. Maybe it's cool if you've been doing it all your life, but putting an outfit together to showcase your new found look is lame, and obvious.