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.
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.
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.