Find out styles and attitudes. Watch Dogtown documentary again and take notes.
Look into vintage skaters more. Who were the big names?
Think about the demand for vintage style boards. Is the there a market for it? Research into the popularity of it nowadays.
Is there rivalry between old school traditionalists and the modern skaters?
Think about creating rivalry in the brand, one half of the logo could get bigger the more clicks it get on the website. This could encourage more people to come to show what is more popular.
Possibly create some kid of avatar for each half of the brand.