We know your mom shops for you sometimes. Hello mom! We've got a list of kid friendly skateboarding gear as far as graphics and company image go to give you some ideas on getting little Timmy fitted and kitted.
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.