Santa

The Santa hat nears the top of the list in terms of comfort, but its gaudy style keeps this from being anything other than a seasonal hat. It can only be worn at three separate occasions: Christmas time, “Christmas in July” themed events, and other themed parties throughout the year including Halloween; although, in my experience, I have never seen anyone dressed up as Santa to go trick-or-treating. It performs well keeping one’s head warm, although it has no ability to block out the sun, and it can be worn in all 360 degrees. Sunglasses make for a very casual vibe, and also look at least somewhat decent compared to other styles. The santa hat is one to keep tucked away except for special occasions and that certain time of year, or if you’re a little weird and very desperate you can wear it around the house for something warm and comfortable.