In The Elder Scrolls V: Skyrim for the PC, PS3, and Xbox 360, pickpocketing is one of the easiest skills to level up, and can be extremely lucrative.
Level Pickpocketing With Skill Trainers
A very fast trick to leveling up pickpocketing quickly is by spending money on skill trainers, and pickpocketing the money back. Any time you spend money on a skill trainer, the money they take from you goes directly into their inventory, which means it can be stolen back from them. Stealing large amounts of gold gives you a large amount experience for the skill as well, making this process extremely fast for leveling pickpocketing.
Level Pickpocketing With Pots and Baskets??
Yes, you heard right. Another “cheap” method is to pick up baskets or pots and put them onto the heads of all of the nearby npc’s so you can pickpocket successfully. To pick up items, you simply hold the button that y0u would normally press to take the item. For example, on the Xbox 360 you press and hold the A button to pick up items.
Level Pickpocketing By Stealing Expensive Items
If you want a less cheating feel, then look into random npc’s pockets until you find rings or amulets worth decent amounts of gold (opening an npc’s pockets isn’t a crime). The higher the value, the more skill you get for successful picking. Follow that npc around until they are alone in order to successfully pickpocket them, or simply find their house and break in at night to pickpocket them as they sleep.
Make sure to save your game before your pickpocketing attempts so you don’t end up going to jail.