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.
Cruiser boards usually vary in shape from traditional street boards and can vary widely in width, but generally are shorter than about 34 inches. Cruiser completes come with softer wheels, too. Softer wheels are an easier ride. Cruiser boards are generally not for doing tricks. They're transportation like longboards, but don't have the uncool factor that longboards got stuck with from the street skaters.
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.
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.