I would look like a twerp, because I'm too roundshouldered and dumpy to wear the sort of winter top those boots need to balance them.
If you can wear a big fur hooded Parker or Gillett, a coat with a big fur collar or a big chunky sweater and scarf and maybe a hat you won't look a twerp.
If your feet look ready for snow, but you wear my fairly fitted, suitable for September or April quilted black jacket, you will look a twerp. Add a Arran hat and chunky scarf and you won't.