Totally - that's how Hipsters dress when they go sailing. But I have to say it always creeped me out. The washed out colors, the attentive looks at the buoy, the body language of the helmsman - somebody just put their beer down and went, "That's not right".
I had a copy of Hopper's The Sailboat in my room as a kid.
I took it as an admonition to never screw up my navigation. I always interpret the caption as, "oh shiiiit".
On my boat, I want a pastoral scene. Some guy running a plow or something where they don't know what an oar is. Because...