Winter Hats That Make Me Look Stupid

Now as many of my close friends know, I am always complaining about the cold.  And it being the dead of winter and at least -30 degrees outside, I decided it was time to buy a winter hat.  But what kind?  You see so many women walking around town, donned in their stylish arctic headwear, they make it look so easy.  But is it?.... NO!

Instead of looking like this....

I get this...

There clearly has to be some arcane magic to looking good in a hat that is fiercely guarded so that us mere mortals are doomed forever to look ridiculous.   Or maybe Ive just got on odd shaped head.