I'm not American, so I haven't experienced the Halloween outfits you are talking about, but your description did remind me of someone, namely Austrian émigre Hollywood director Fritz Lang, especially the monocle part, which he made into something of a brand.

And it seems like the sources agree. In Fifty Hollywood Directors, Routledge, 2014 (ed. Suzanne Leonard,Yvonne Tasker), p. 135 it said that "few directors (perhaps with the exception of Erich von Stroheim and Josef von Sternberg) have come to epitomise the stereotype of 'the genial German director' as much as Fritz Lang: his aristocratic appearance replete with monocle, riding boots and jodhpurs and reputedly fully conforming to the idea of the autocratic and obsessive perfectionist who was admired and hated in equal measures" and "Throughout his life Lang cultivated this almost caricatured self-image".

And it seems true. A simple google image search makes it clear that you will be hard pressed to find a picture of Fritz Lang without the monocle (he didn't always wear riding boots and jodhpurs it seems).