Hello Jay,
Sorry to be blunt, but get some socks like Dennis's for wearing outdoors in grassy places, if nothing else. You look dorky because you're risking chiggers and ticks and all sorts of bug bites standing there in the grass by the outhouse in ankle socks.

Think more practicalities, less fashion.
And then, watch, the higher socks will grow on you. You'll like the feel of you ankles covered and you'll end up wearing them just like that to bars and movies and such. Over time you'll base these decisions less on what looks dorky and more on what you can get away with.
Sonia -- a guy in some previous life