Shorts are like the nickname of pants. Some people can run a good nickname and it's not weird at all. Other people you try to stick a nickname to and it just doesn't feel right. Take your approach to wearing shorts while skating with this caution. I still never wear shorts while skating, but for the chill out tent, shorts are mandatory. That's why we got these.
My earliest memories of the bucket hat taking over skateboard headwear was when Earl Sweatshirt started to run them constantly in the early days of Odd Future. These days, everyone has to have one in their headwear lineup.
We get an above average amount of travel in on our skateboards with all these events we do around the world with The Boardr. Here's a small sample of what we use to make the trips that much more comfy.