It's good that your parents are cool with it. It makes it so much easier when it isn't treated as an act of rebellion.I have found that if you follow the clippers with a good buzz with a Norelco shaver before you hit the shower, it makes it much easier to shave with the blade, and less likely to nick the skin. But, go lightly with the electric shaver until your skin toughens up, or you will get razor burn from the electric.As for cold weather... one word... HOODS... I find a hooded sweatshirt more convenient than a hat. Just flip it up when you get cold and flip it down when you get warm. With a hat, you are more likely to leave it laying somewhere. In really cold weather, a hooded parka is a must.
Hoodies aren't really my thing. I got a beanie from the 99-cent store though. I love my beanie already!