You'll be fine. I would expect that the SWK Standard might not see much use if it gets below 45 or so. I spend all last winter in Chicago and my SWK Standard, my lightweight Pride of Scotland, and my AK were the only ones that did not get worn. And I think that hose pulled up with Doc Marten type boots looks fine. That is all I wore for normal work attire. If I was going somewhere more formal, then I might add flashes and wear wingtips.