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.
Do you remember when fitted hats and six panels got knocked off everyone's heads by the big five panel trend a few years ago? I think it was the early days of Odd Future and Tyler that really helped kick off the change in domepiece attire. These days, five panel hats still run strong.
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.
Why are these called trucker hats? Do truckers sweat through the head more than your average cut of society? Nope, I think we need to take this one over and officially change the mesh top lid to being called a skater hat. For as long as the three decades we've been around in skateboarding, these hats have always been around.