Land or lake, a man can never have too many dark blue shirts in summer. Particularly in linen, where lighter colors are often too sheer to wear without an undershirt that defeats the purpose.
I like my navy shirts with tails, as they are worn tucked into cream or tan colored trousers. The pullover cotton knit versions are without pockets, but the linens close down the front and have two buttoning chest pockets for my sun and reading glasses.
The illustration reminds me of my childhood, on glacier-carved lakes in Northern Wisconsin where we sailed snipes and cats. The cats didn't have a deck so they were challenging in a stiff breeze. If you put the rail in the water you'd swamp the boat, and that was an assured way to lose a race.
The illustration takes liberties, of course. Our tiller man would never be seated on the low side of a heeling boat, and it's not likely that the blonde would be keeping his pipe lit in that wind.
But they show the virtues of navy shirts on land or lake.