Each year I find myself in the 6 month stretch of winter here in MI. The snow & cold are unavoidable, so one small way I bring in some brightness is by intentionally matching my gloves to my boots.
I always opt for leather as they are much warmer than the knitted variety, and I recently picked these snow boots up from Poshmark. The silver is neutral, but pops against the darkness of the season.
Another fun duo to match are a hat and scarf. They could be from the same set, or a similar color/print.
Basically your goal is to cut down on decisions if you have to rush out to shovel or bundle up during a storm. Ease in dressing for the cold may not be as simple as the heat, but it is doable and can be enjoyable too!