In the early days of skateboarding t-shirt design, it was common for t-shirt graphics to be on the back, with a small hit on the front pocket space. As the golden era of skateboarding began in the early 90's, literally every single t-shirt made had the graphic on the front. These days, the graphic on the back is starting to make a comeback, pun and all.
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.
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.
Sunglasses are all over the spectrum, literally, in skateboarding. Some are $10, some are well into the hundreds. We've got most of the spectrum to choose from, but it's up to you to figure out the appropriate time and place to run these. Certain people can pull them off at night or in the club, while others just don't look right even with them on in the daytime.
The six panel hat is a classic and still holds strong today even though five panel hats are more common. Who would have ever thought the six panel would have been dethroned as the champ of headwear that had a good solid two decade run in skateboarding?