In my opinion, just do what makes you feel comfortable, but if you want to adjust and want to get out more this time of year, maybe you need someone to help you out with it. You can’t tackle every emotion alone, let alone slip into a depression. Find someone who loves this weather, someone you can have fun with, it’ll take your focus off of being cold (that’s the goal anyway). Or option two, take something you absolutely love doing and can’t live without i.e. photography and
apply it. Come up with a reason to be outside. I’m not saying pack your bags and go camping, but start with something little.

(Sounds terrible but..) The few times I need to walk through the city when it’s windy and cold, and air seems to creep its way into every opening in my coat, I will admit, I wish I were at home in bed. People say stop look and listen, no need to stop, just a glance over to the right is a woman fumbling with her inside-out umbrella, or the man on the left trying to catch his fly-away papers is enough for me to giggle, forget that I’m freezing, and suddenly enjoy the weather.