So looking at history, we see that most pickpockets weren't adult males like the protagonists of Assassin's Creed and Dishonored, but instead were largely children and women. However, Skyrim was extremely on-point with its characterization of another aspect of pickpocketing - that of the "schools of vice." In Skyrim, the player can't become a truly successful pickpocket until he or she joins the Thieves' Guild, thereby gaining access to the organization's training as well as becoming subservient to its hierarchy. And in both Skyrim as in real life, pickpocketing is only an initiation before the apprentice thief moves on to bigger and more serious crimes.
Ingenious Historical Methods
"No cleverer pickpockets exist than in this country," wrote Swiss traveler Cesar de Saussure, reporting that thieves had stolen his snuffbox. He was especially vexed because he'd taken precautions: "[I] placed it into the pocket of my carefully buttoned waistcoat; my coat was buttoned likewise, and I was holding both my hands over the pockets of my coat." Despite this, poor de Saussure never had a chance against the studied tactics of London's buzz-nappers.
Pickpocketing is an urban crime. It requires big city crowds, not only to provide targets but also because the rush of city life gives thieves pretense to get close to their target then disappear into a the thousand other faces. Georgian-era gangs usually targeted large crowds. They favored theaters and parades, as well as the hanging fields at Tyburn, where they stole beneath the scaffold as fellow pickpockets died for the same crime. Having said that, Georgian pickpockets didn't simply stick their hands in someone's pocket, their world was filled with subtle stratagems and fast cons that meant gang members had to be actors in addition to being thieves.
Many tactics involved a team of pickpockets working together, with one acting as a diversion. "Abraham Men" would feign madness to steal attention away from their accomplices. "Confek Cranks" faked epileptic seizures. Sometimes one gang member would trip a gentlemen or knock them down "accidentally," and his accomplices would fleece the victim while pretending to help him up. Others would sneak up on a gentlemen and knock his hat over his eyes, then dive into his pockets when the mark raised his arms to readjust his headgear. In all these cases, they'd hand stolen goods off to another gang member who'd immediately slither away through the crowd. However, the most common and effective group tactic was for the most suspicious-looking gang member to bump into a mark. The victim, thinking he may have just been pickpocketed, would then feel for his valuables, telegraphing their presence to accomplices down the street. Modern thieves have refined this tactic - instead of bumping into people, they simply hang "Beware of Pickpockets" signs in heavily-trafficked areas.
Other criminals used disguises to facilitate their schemes. The most ingenious pickpocket in English history was a woman named Mary Young, alias "Jenny Diver." Jenny had a particularly interesting disguise - a dress that made her look heavily pregnant and included a pair of false arms folded in her lap. That way, she could attend church services and raid her neighbors' valuables without drawing suspicion to herself. The pregnancy disguise also made an excellent distraction when she'd pratfall in front of a crowd, causing a huddle of people to rush to her aid and help her up (without realizing her friends were stealing their watches). But Jenny was far from the only pickpocket to use a disguise. Stylishly-dressed thieves known as "Spruce Prigs" would blend in with the aristocracy at society balls and the opera, where the better element mingled dressed head-to-toe in luxury goods.