I'm a contractor and I prefer layering multiple sweatshirts over a heavy jacket. Most of the year I'm just in shorts and a t shirt, then when it's cold I'll add a sweat shirt. When it gets colder, sweat pants, a beanie, wool socks and another sweatshirt works great. Really cold, I'll add another sweatshirt and another beanie. For this latest cold snap that had a low of 18 and a high of 31, that was plenty.
I have a heavy 20 year old Carhartt jacket that I might wear half a dozen times a year to work. Usually it's too bulky and heavy to keep long longer then setting up my tools or unloading my truck. It's a great jacket that's nice and warm, but I don't like how much it weighs.
My wife likes to give me jackets for Christmas. I try to wear them just to make her happy, but now I'm having to deal with all the space they take up in my closet. I hope I don't get another jacket this year. She also likes to give me gloves, beanies and wool socks. Winter is only two months here at the most, and even then, we have plenty of days in the 60's that I end up in just a T shirt and shorts.
Will your son wear a new heavy jacket? Does he want one? Or would a good set of boots be more useful? I go through shoes quickly.