Cool ma-1. Buzz Rickson?
The fit is a little incongruous––a military repro jacket works with raw denim, but not necessarily a gingham shirt and those sleek shoes. It's half CM casual, half SW&D uniform. Feels weird. I think you could try this with chunkier boots (black? reverse leather? waxed?) and jeans that aren't cut like CM trousers. Get some stacks, maybe a straighter lower leg. And like, a white tee.