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The description of the Gloves of Thievery (DMG, p. 172) says:

These gloves are invisible while worn. While wearing them, you gain a +5 bonus to Dexterity (Sleight of Hand) checks and Dexterity checks made to pick locks.

The Arcane Trickster rogue's Mage Hand Legerdemain feature (PHB, p. 98) says:

Starting at 3rd level, when you cast mage hand, you can make the spectral hand invisible, and you can perform the following additional tasks with it:

  • You can stow one object the hand is holding in a container worn or carried by another creature.
  • You can retrieve an object in a container worn or carried by another creature.
  • You can use thieves’ tools to pick locks and disarm traps at range.

You can perform one of these tasks without being noticed by a creature if you succeed on a Dexterity (Sleight of Hand) check contested by the creature’s Wisdom (Perception) check.

In addition, you can use the bonus action granted by your Cunning Action to control the hand.

Technically the gloves are on the hands of the character, but would the bonus they provide also affect the additional actions you can perform with this special feature granted by being an Arcane Trickster?

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  • \$\begingroup\$ The description of the Mage Hand Legerdemain feature is different from how it's stated in the PHB. I've edited the fixed quote into your question. I don't think it changes your interpretation, but if it does answer your question, you may want to revert my edit and then leave your own answer with your revised understanding of the combination of the two. \$\endgroup\$ – V2Blast May 16 at 3:39
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Is the character wearing the gloves? Yes. Is the character making a Dexterity (Sleight of Hand) check or a Dexterity check to pick a lock? Yes. From a plain reading of the quoted rules, the character therefore gets the +5 bonus from the gloves.

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  • \$\begingroup\$ The description of the Mage Hand Legerdemain feature in the original post was different from how it's stated in the PHB. You may want to review the revised quote to make sure your answer is still valid. \$\endgroup\$ – V2Blast May 16 at 3:38
  • \$\begingroup\$ I think it stands: the Mage Hand just extends the range of your thieves' tools, and the gloves don't read "While wearing them you gain a +5 bonus to checks made with your gloved hands", just "you gain a +5 bonus to checks". The plain English interpretation is still "is the character wearing the gloves? yes. is the character making a check? yes. therefore, the character gets the bonus". \$\endgroup\$ – minnmass May 16 at 3:50

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