I am a big love of hats. I probably own way too many, but I can't resist. When I see an adorable looking hat I'm drawn to hit like mouse to cheese (that's a horrible simile). The problem with hats though is that they can give you hat hair, which no one wants. It makes lots of hairstyles not doable because when you take off your hat you get frizzy staticey (apparently not a word) hair with a weird line where your hat was pressed into your scalp (although, if your hat is so tight I suggest getting one that isn't).
Therefore, to help make your winter easier, here is a video where I show you three hat friendly hairstyles. I think these look great with or without a hat, and they keep things interesting so you're not wearing a same thing every single day.