It always amuses me how he keeps holding on to the beanies even in the scorching heat of a Texas summer.
And that although he is already running hot as it is - the head will just conserve the heat even more.

But we all know it's kind of his security blanket. So if it makes him happy - he should go for it.
Plus of course it keeps him from needing to style his hair and it doesn't get in his way. Which we can probably all relate too.
Although every time he takes off the hat, he basically just runs his hands through his hair once and it looks perfect.
Wish I had that magic power. It's clearly Supernatural.