I ride my bike to work and back all winter long. I see winter as an adversary that shall not be allowed to take away one of my favourite things, and I have figured out how to stay comfy and enjoy the ride in any weather. I only failed to ride in on 2 work days last winter thanks to truly impressive weather, and I'm gunning for a flawless record this year.
Since many motorists are either made nervous or angry by my presence in the off-season, I try hard to look like a well-equipped, serious and safe cyclist. I drive a car too, so I can relate to worrying that some idiot on a bike is about to do something stupid or dangerous that results in me squishing them flat. I am well reflectorized and lit in the dark, I wear a good deal of cycling-specific clothing, hold a nice straight line and ride in a predictable way. I even use hand signals. I am winter cycling's responsible, nerdy Ambassador. Grudging respect and acceptance is my goal, not looking stupid. Thankfully, for those wishing to expand their repertoire of dorky behaviours, others are happy to lead by example.
Tip #1 - Get drunk first. Have you ever tried to ride a bike drunk? No? I strongly advise trying it in winter if you're going to try it at all. Go hard or go home, as they say. Like the drunk dude who crashed repeatedly in the greasy snow on a very busy street right in front of me last year. He was awesome.
Tip #2 - Be woefully unprepared. Like the rugged bare-headed and handed men both young and old who ride recklessly in whatever direction might offer the best chance of keeping most of their frostbitten ears from falling off or allow them to remove their clenched, frozen hands from the bars upon reaching their destination. They are legion, at least in early winter. I can only guess the resultant injuries prevent any more gloriously stupid rides as the season wears on.
Tip #3 - When you see that ultra-polished ice that occurs at stop signs where drivers have spun their wheels, especially 4-way stops, insist on "taking your lane" to ensure your safety and fair treatment as a vehicle at the intersection. When you come to a stop, confidently put your fancy new winter cycling boots down as your bike attempts to slide out from under you. Discover that the hard plastic cleats of said boots do nothing on such ice. With agonizing slowness, carefully tip-toe yourself and your bike out of the way while impatient motorists on their morning commute watch with disdain and think "now look at that jackass. For somebody so well dressed, equipped and reflectorized, he sure is stupid."
Ambassador. Yay me.