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When does the +10 to Disguise take effect?
I understand that the +10 works when created, but if you are using the hat to change your appearance, anyone looking will see what you created, and once they penetrate the spell, you lose the +10.
So either, they see what you want them to see, voiding the need of a disguise check, or they see through the spell, completely negating the +10 to the disguise check.

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The +10 is to your Disguise check to pass as whoever you're disguised as.

The checks that are made when using the Disguise skill are described here. To sum up:

  • When you put on a disguise (magical or not), the DM makes a secret Disguise check for you to see how good it is. This result stands for the entire time that you're wearing that disguise.
  • When you're seen by someone who has a reason to be suspicious, or who personally knows the person you're disguised as, they get to make a Spot check against your Disguise check result. If they win, they become aware that you're faking.
  • If you meet someone who's just generally alert for suspicious activity, they get a Spot check also, taking 10. This effectively sets a fixed Disguise DC for being in areas that are patrolled by guards.

Disguise covers both costuming yourself as someone and imitating their behavior (their walk, manner of speech, etc.). A Hat of Disguise or other magic to change your appearance will do the first part for you, giving you +10 to your Disguise check, but it doesn't make you into a great actor. (From the disguise self spell: "The spell does not provide the abilities or mannerisms of the chosen form...") You do still have to make the Disguise check and other characters do get Spot checks to recognize you.

All of this is separate from the Will save against the illusion, which follows the general rules:

Saving Throws and Illusions (Disbelief)

Creatures encountering an illusion usually do not receive saving throws to recognize it as illusory until they study it carefully or interact with it in some fashion.

A successful saving throw against an illusion reveals it to be false, but a figment or phantasm remains as a translucent outline.

A failed saving throw indicates that a character fails to notice something is amiss. A character faced with proof that an illusion isn’t real needs no saving throw. If any viewer successfully disbelieves an illusion and communicates this fact to others, each such viewer gains a saving throw with a +4 bonus.

So, every sentry and shopkeeper that sees you walk down the street in your magical disguise doesn't get a Will save to beat the illusion. To get a Will save they have to study it carefully (which shouldn't happen unless you've already been caught, or you have to deal with someone very paranoid) or interact with it.

Interacting with the illusion might happen in casual contact, though it's avoidable. If they do disbelieve the illusion, then you're probably busted; good luck explaining why you were wearing an illusion of someone else's face.

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For example, you use a Hat of Disguise to try to look like a guard and attempt to enter a restricted area.

The guard outside observes you, makes the save against Hat of Disguise, and fails. You have a +10 bonus on your Disguise check while trying to look like a guard. You do not automatically look like one just because of the illusion (for example, your memory of what a guard looks like may be faulty and you might get a detail wrong).

If the guard makes the save, then you don't get the +10, and hopefully you have attempted a non-magical disguise as well, or else have fun.

If you are doing this while observed, then you really don't get any sort of Disguise check, unless you could somehow bluff your way past explaining how you shifted appearance.

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