Well SlycatCrossing has a point, and im sure you will get accustomed to it in some measure, but depending what weather conditions you encounter in your life, it may never leave. My dad has been bald for over 30 years and he still gets a frozen head when ever he goes out in the cold winters or gets near a AC in the summers. I mean, your head and feet are the top places that absorb or release heat, so when you shave your head youre basically baring a huge sponge to the wind.
If youre normally in any weather under 50 degrees, you will likely feel a cold chill on your head fairly frequently. Where i live, in the winters it can be single digits fahrenheit for weeks on end, and theres no escaping a frozen head when you walk out the door without a hat. Same with our summers, it peaks around 85 consistently for the summer but if you walk into a air conditioned room, youre going to feel cold on the north pole.
Just personal knowledge from my dad and an array of bald men ive known my whole life. It seems to be a lifelong struggle to keep the head warm or cool when youre bald!