Most Helpful Guy
I wonder if He's planning on taking you somewhere, where your going to be outside in the cold weather? I don't have any suggestions but I will share with you how I dress at work and why. Where I work, they turn off the heat. Because of that I wear layers. T-shirt, Flannel Shirt, and a Coat. That way as I work, I warm up. As I warm up and remove the coat. If I'm still too warm, I remove the flannel shirt. When I go on break I put the flannel shirt back on. If I'm still too cold I put the coat back on. Since you don't know what He's got planned, you might want layers so that you can dress up or down on the fly.
Most Helpful Girl
Sweater dress, leggings, cute booties with a warm sweater, leather jacket, or a coat or a coat and maybe a cute beanie. Cute, comfortable, casual, and laid-back.