I hate the cold and I have perfected staying warm to the point that I no longer feel cold around winter.
I suggest getting a sweater/jacket that has warm material sewn on the inside; there are several types that use different material on the outside that they can be worn for different occasions. You can also get tees and button shirts that also have warn material sewn on the inside that you can wear underneath said sweater/jacket.
Finally, if you can get your head around a beanie with climate controlled fabric, you should be ready for anything.
...Except snow, but that's a topic for another day.