Ideally, you never wear a hat backwards unless you're the catcher for a basebeall team or you're the frontman of Limp Bizkit. You said last year that you still had your original red hat from the 90's You should post a photo of it! — Matt (@mt2oo8) If you're just one of those people that loves having their head covered, but hates the idea of keeping the sun out of your eyes, you are allowed to practice this style faux pas into your mid-twenties. Making Your Own Wii Theme Songs. After that, it's time to turn your hat forward and look to the future. The backwards hat is a sign of cheeky, somewhat douchey youthful rebellion, much like hanging out at the gas station smoking cigarettes and rolling your eyes whenever an adult give you useful advice. Once you become the adult giving said advice and you start telling kids to stop smoking and go home, it's time to give up the backwards hat.