I live in New England so the main problem is unpredictability . It can be warm and lightly raining one minute , and then can start snowing and turn into a blizzard . I have two winter coats , one more durable , waterproof , and machine washable for everyday use , and another wool coat that ' s a little more fancy for formal events like holiday parties . I always layer when it ' s cold , so a hoodie an outer coat . I keep gloves in my coat pocket , and sometimes keep a pair in my car if one pair gets wet when shoveling or clearing snow off my car . I always have a hat , and a fleece scarf if it ' s very cold . I have a sturdy pair of winter boots and a more casual pair of ankle boots . I ' m eyeing a new durable coat this year as my old one is probably 10 years old , so I ' m thinking of getting one from LL Bean . Style kind of goes out the window outdoors , but indoors I tend to wear more sweaters and circle scarves .