@Otomatrose excellent point. I'd still consider it fitting given that it suits the Medic's backstory and character. He's originally from Stuttgart and kind of a shady/phony doctor. The hat's name doesn't make sense at all, like you said, just like the medic's 'medicine'. A phony doctor is now a phony sailor :>

or maybe it could just mean that he's a skipper who happens to be from Stuttgart lol

I like the hat a lot but the name feels a bit off.
I know Stuttgart is like THE german city that starts with an "S" but it's in the very south of germany, far away from the sea. Sure they have the Neckar flowing through but I feel like there could've been better naming options for a german reference.

Dope hat, but do wish you were to also include a version without the ancher icon

Would work as a great priest esc headgear

Awesome set