Boat shoes generally bug me when they are worn with jeans or anything semi-formal. Suit and boat shoes I have seen before, ew indeed. Other then that, whatever. They are good summer vacation shoes though, especially if you own a lake or beach house or visit one frequently.
some people who have actually given thought to their clothes still like that rugged classic american look.
It isn't rugged when all the clothes look brand new out of the box and the guy is clean shaven with perfectly manicured nails.
The guys often look like a fish out of the water. That's what makes me cringe on the inside. If a dude can pull it off well I don't care what his profession is, props for that. That can go for any kind of clothing aesthetic, not just work wear.