My first winter here, so I am a rookie. I would have jeans and or long pants along with sweatshirts. It can get cold overnight, so if you are an early riser and out and about , I would have at least one heavy jacket, scarf and someone told me some people wear mittens.
I also keep a light jacket in the car as some restaurants are cold because the A/C is overwheming like Toojays.
You get so used to being warm that when the temperatures drop, it feels colder.
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"It doesn't cost "nuttin", to be nice". 
MOM
I just want to do the right thing! Uncle Joe, (my hero).