The Elder Scrolls V: Skyrim Hints

Pickpocket

  • 1 of 4: This is a very easy skill to practice. Just crouch down next to someone, quicksave, and then try to pickpocket something from him. If you get caught, quickrestore. If you succeed, exit the pickpocketing screen and quicksave. (Note that whether or not you're seen affects how hard it is to pickpocket items, but it's usually possible -- even if your victim is looking right at you.)
  • 2 of 4: The more valuable an item is, the more skill practice you'll get for successfully taking it. The downside is that you might have to quickrestore and retry many times to get it. It's usually worth the trouble, though. (Just make sure you're not wasting time trying to get an item that has a 0% chance of success.)
  • 3 of 4: You can pretty easily get your Pickpocket skill up to 100 by using the carriages at stables to ride around and visit all of the cities. Pickpocket everyone in each city to get lots of practice and loot.
  • 4 of 4: Note that reverse pickpocketing (where you move something from your inventory into the other person's) will also get you skill practice, so you could keep pickpocketing one or a few items back and forth on one person. However, the skill progress will be slower, and you won't end up with any new loot.