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The Elder Scrolls V: Skyrim Game Add-Ons (DLC) Hints
Talk to the face sculptor in the Ragged Flagon.
1 of 4: You can get this objective by overhearing someone talking about it, or by asking an innkeeper for rumors until it's mentioned.
2 of 4: The Ragged Flagon needs to be visited early on in the Thieves Guild faction quests, so you might as well join up if you haven't already. See the main Skyrim hint file for hints on those quests.
3 of 4: Once you reach the Ragged Flagon, talk to the woman named Galathil to finish the objective.
4 of 4: From then on, you can pay Galathil 1000 gold to let you totally recustomize your appearance. Note that you can't change your name, gender, or race -- just your appearance.