Nothing is more comfortable than a plaid, flannel shirt in cold weather, especially under a leather jacket. I was able to wear one of my plaid flannel shirts so far this Winter. I do not get much use out of them but cannot toss them out of my closet.
Here's a perfect way to wear gray (or any color that no longer suits you). I totally love the way the pink draws attention to your face & your middle (without showing much). Personally, I would replace the turtleneck with the same color and type top.