I'm just going to be very straight forward...

Be as cool as Steve McQueen and get a thick ass wool cowichan sweater.

Over 30 years after his death and he's still taking us to style school.

It can come from anywhere.

Tonight as I sat at a local Taproom. I notice a man siting at the table next to me who is wearing a baby blue cashmere sweater, light wash jeans, thick grey wool socks, and red Chuck Taylors. It was a look that I had to do a double take on. It was very casual, but very impressive.
Just goes to show inspiration can pop up anywhere.

In–vest

So I was remembering an outfit I threw on last year. It was a typical winter day in Northern Michigan and I wanted to class up my usual quilted down Patagonia vest, so I put my grey wool blazer over top. I really liked the way it looked. So I go into the shop I worked at and one of the customers said to me "Doesn't the the blazer go underneath?"
I laughed it off and walked away.
It wasn't really until lately that I had been seeing such a look on multiple street style sites which gives me a little smirk if satisfaction.
Yeah it's cold during the winter months, but that doesn't mean that all you are able to wear is are insulated, down, waterproof, wind proof... You get the idea. Things can be altered. If you have a cardigan and a pullover sweater that you like then wear them together. Winter gives you the opportunity to experiment with a ridiculous amount of layering.
At least that's the case in Michigan.