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For those unfamiliar, a Circlet of Human Perfection is a magic item from the Waterdeep: Dungeon of the Mad Mage adventure (p. 30). Its description reads:

The circlet transforms its attuned wearer into an attractive human of average height and weight. The circlet chooses the physical characteristics of the form, such as age, gender, skin color, hair color, and voice. Except for size, the wearer's statistics and racial traits don't change, nor do items worn or carried by the wearer. Removing the circlet ends the effect.

If I allow my skeleton created with Animate Dead to attune to this item will they be able to blend in perfectly? What about their ability to speak?

The language trait for skeleton reads that you can't speak, but the circlet reads that you gain the voice of a human. Do the racial traits staying the same supersede the gaining of the voice?

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    \$\begingroup\$ Are you considering a skeleton a race or a creature type? \$\endgroup\$ – KorvinStarmast Jul 30 at 19:31
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A skeleton cannot attune to the circlet

The circlet's description says:

This circlet is an uncommon magic item called a circlet of human perfection. Only humanoids can attune to it. The circlet transforms its attuned wearer into an attractive human of average height

Only humanoids can attune to it, but a skeleton creature type is Undead, not Humanoid.

Otherwise, almost any creature could be transformed into a human with this circlet, which I believe wasn't the item's authors intent.

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    \$\begingroup\$ Good catch, turns out reading the rules explains the rules. \$\endgroup\$ – Lucas Wood Jul 30 at 19:50
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    \$\begingroup\$ Just need to somehow give that skeleton 13 levels in Rogue so it can gain the Use Magic Device feature! \$\endgroup\$ – dhmstark Aug 1 at 17:25
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The item description says:

The circlet chooses the physical characteristics of the form

which implies that the circlet has some kind of will of its own, so maybe it decided that the skeleton counts as humanoid?

The rules here are a little limiting by only allowing a creature to be of one type at a time when a human, elf, dwarf, etc. skeleton is still the skeleton of a humanoid creature.

Sense dictates that skeletons count as Undead and Humanoid. They are Undead Humanoids.

On a personal level - I think your idea is really great, and would make for terrific story telling. You could even amp up the idea of the sentient circlet, if you wished, by suggesting that it has been somehow coerced, persuaded, or bribed into working on the skeleton. Or the skeleton could be just as surprised as the players the players that the effect worked. There's so much you could do with this so I'd hate to think that you discounted the idea on a technicality.

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