Mask of Many Faces + Disguise kit combo?

[Foolwise]

My character has Mask of Many Faces for at-will Disguise Self castings and also proficiency with the disguise kit from the Entertainer background. Rather than let MoMF render the prof obsolete, I have come up with an idea. Basically my character would develop a physical disguise to hide her drow heritage, then use MoMF to create the same disguise magically. Maybe have the magical disguise enhance certain features, so that if a creature succeeds their Int check against my Disguise Self spell, those 'enhancements' fade away, leaving the same physical disguise in place. It also provides a failsafe against Dispel Magic.

In my mind, the only logical way a NPC would have reason to doubt the physical disguise after seeing through the magical one is if they had some evidence to my drow ancestry. Perhaps they overheard my companions or myself refer to it in passing, for example.

How would you play this out at your table?

[Segev]

It's a good idea. You might even make the underlying disguise notably different, possibly with an ugly scar or few, to explain why she uses magic to pretty herself up.

[Tanarii]

Disguise kit uses when you have at-will Disguise Self:
- create a disguise that (may) stand up to physical examination, at least better than DS
- Disguise other party members
- gain advantage on related Deception, Intimidation, Performance or Persuasion check (if your DM uses Xanathar's)
- Spot a disguise being used by someone else (if your DM uses Xanathar's)
- Copy a humanoids appearance (if your DM uses Xanathar's)

Worth noting that Disguise Self doesn't explicitly call out that you can make yourself look like someone's else specifically, but it does say the details of the appearance are up to you. So most likely any DM will rule it can, making the last point superfluous.

Disguising your Drow heritage would imo take a fairly serious disguise. At the minimum lots of face paint, hair dye, and long sleeves with gloves.

[Segev]

Disguising your Drow heritage would imo take a fairly serious disguise. At the minimum lots of face paint, hair dye, and long sleeves with gloves.

A well-made mask could reduce the amount of face paint needed, potentially. Latex isn't a thing in most fantasy settings, but very high-quality leather with any stitching well-hidden or disguised as scarring could cover the majority of the head and even neck, and even provide an attached wig of real hair. (You may want to shave bald beneath it.) Or you could make it a very elderly face, giving you more wrinkles to hide stitching in if needs be, and also letting you run your drow hair through it as "old (wo)man white" instead of "drow white." This could ALSO explain why you use disguise self all the time to look younger and thus better-looking.