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.
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.