1. Always lock on to your target. 2. After your lock on you just need to get not too far and not too close to your pickpocket target 3. While you're walking to your target hold the pickpocket button (you will have your hand out so don't bump into anybody, you might just steal from them or something) 4. Now that your hand is out, just keep on walking slowly until you get to the belt of the target (there is a pouch on the belt that it helps to aim for).