How do you pickpocket on assassins creed

In Assassin's Creed 1, you can only steal throwing knives from henchmen. They're big, burly dudes wearing brown leather and they have a pouch on their back like a fanny pack.

In Assassin's Creed 2, you can just hold the "Slow Walk" button and walk into anyone you'd like and you'll pickpocket a small amount of money from them. There are three very distinct types of people as well: the poor, the middle class, and the upper class. The three different classes will give you different amounts of money. You can tell what they are by the clothes that they wear.