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I use a beanie (I have one with the Silver Fern on, its actually considered patriotic to wear something with a Silver Fern on, cos its the national symbol of New Zealand), a cap (a red one) and a hoodie (on my Skaters sweatshirt)
I don't wear hats full stop. I've just never been fussed with them, and my head doesn't get cold that easily, so I've never needed to wear one to be honest...
I wear hoodies in the winter, they keep your face warm XD. I usually wear a cap if I've just woken up and my hair looks scruffy but I can't be bothered to fix it.
I wear beanies during the winter and when my hair is long. It helps my hair from poofing up and getting frizzy, which it does when I let my hair get long and do nothing to it. XD
I have a hat. It's not really a cap, it's just a hat. I wear it when I listen to music. It's an old habit, and you know how hard old habits are to break. o.o;;;
and it's handy when I'm on the bus in the morning. It blocks the sunlight. XD