Do you get new winter outerwear every year? Many years I have gotten new hats or scarves even though my old ones were not worn out. I liked getting something new so I would just donate the old pair so I didn't have a pile up of things I did not wear. I think hats and scarves are especially fun to switch out for new ones, just to mix things up, and usually after just one or two years, they are till in very good shape and can be given to someone else who needs them.
I do typically buy a few new items of winter gear every winter season. Not a lot typically. Because I usually buy stuff that lasts and the winters around here are typically pretty mild, though that has changed a bit in recent years with a bit more snow. Typically I buy gear from Columbia and The North Face.
Not every year, no. A lot of the time with my budget and other things that take priority, I'd rather be careful with my items and keep them good and in my wardrobe, instead of buying new each season. Sometimes what I'll do is pick things up as the season is ending, though, to stock up for the next winter.