I know the Winter Bash is temporary but for next year, could premium hats be added to the mix. Ones that you can use your reputation to buy? Just thinking of ways reputation could be used for more fun hats or variations of the same hat.
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Actually, this is already in the Winter Bash FAQ:
All joking aside: we don't like using reputation for anything besides "Look at my awesome" measurements. You can't buy swag or flair with rep -- hats are no different. Remember: hats are badges you can wear!
Finally: we have seekrit hats. They're basically the "premium" hats you describe. :)