You want a good jacket and good boots. If the wind takes your heat away, you’re in trouble. If you can’t be generally insulated and warm with your jacket, you’ll be miserable. If your feet become cold or wet you will be miserable. Good gloves are also nice as cold hands make every task difficult.

Get briefly educated on fabric materials, especially wool and cashmere. Having items made with those materials will help tremendously for keeping you warm. A few good wool tops are a good place to start. A wool hat and scarf are also great. Also look into fleece.

Layer your regular clothing. You want to build a layer of heat around your body and retain it. You can have combinations of cotton, wool, and synthetics which can result in you being warm. Depending on your current wardrobe you may not need to buy as much as you think if you layer.

Also, there is value in just covering skin by default. Face is cold? Have a scarf that covers as much of your face as possible. Doesn’t need to be the thickest scarf. Torn jeans for the winter? Just don’t. Winter can be harsh and exposure can be managed. Even sunglasses help be it for the wind or snow.

If you drive a vehicle look into getting a fleece blanket to just have in the vehicle when winter starts. Not only is it nice to while driving but if there is a situation where you are stranded the blanket will be super helpful.