To get this achievement, you must have at least rookie 1 REP in the park.
You start out as a prospect and you have to play online modes to reach this rank, and you will gain it quickly (I got it after 2 games on the courts).
Once you are rookie 1 REP or higher and in the neighborhood, head to the "Wheels Bike & Skate Shop" and head inside.
Purchase any vehicle in the store (the skateboard is the cheapest at 60k VC).
Once you are back outside, press LB and choose your skateboard. While moving hold the left trigger and point your right stick in any direction you have an emote equipped to get the achievement.