You may be confused about the ability of shirts. So am i. But as long as you wear a warm enough legging, then there is no need to worry about the weather. And you can also enjoy the flying dresses just like summer.
A black skirt is good in winter for it's color. You can arm yourself with a warm and fashion scarf and a hat also.
You can see from the street style that a grey and dark blue also can be chic. Here is a warm hint that you would better wear it in a fine day. And you know the reason.
On a sunny day, you may pick a stylish sweater to collocate with your maxi or short skirts.
As to the hairstyle, most people would thought that long hair or just the hair flowing on your back is suitable. But a updo will be fresh to be seen in winter too. Make you own choice then.