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Is there any combination of heavy armor and a Dragon Priest mask that allows the Custom Fit perk to be active?

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No, because as stated in @Nelson's answer, Custom Fit is a Light Armor perk.

However, there is an equivalent perk in the Heavy Armor tree called Matching Set:

Additional 25% Armor bonus if wearing a matched set of Heavy Armor.

This perk you can get while using a Dragon Priest Mask. All of the Dragon Priest Masks in the game (including the Wooden one) are classed as Daedric Armor - so wearing Daedric chest, hands and feet pieces along with any Dragon Priest Mask will fulfill the criteria to activate the perk.

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  • As a side note, they also counterintuitively negate the "mage armor" perk when worn. There are mods, of course, which change these to be classed as "clothing" to resolve this problem.
    – CDove
    Apr 16 '18 at 11:52
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No armor involving any Heavy Armor will activate Custom Fit.

The reason is Custom Fit triggers only on all Light Armor. Heavy Armor is obviously not Light Armor.

Custom Fit

25% Armor bonus if wearing all Light Armor: head, chest, hands, feet.

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