Rigging High Heels?

Hello!
I’m rigging a character that wears ankle boots. I made a “heels up” pose for the character with her rig and modeled my shoes around her feet in that pose. When I parent the shoes to the rig with automatic weights it deforms the shoes from the way I modeled them, so it’s kind of “doubling” their deformed shape.

Is there a way for me to attach the shoes to the rig in the “heels up” pose without them being deformed? I’d like them to deform with the rig afterwards, but I want them to be in the shape I modeled them when the character is in her “heels up” pose. I’m fine with them being deformed from the original shape when the character goes back into her default pose, if that makes sense.

Here are images illustrating the issue: https://imgur.com/a/YrNAHf1

It’s not impossible, but it’s a pain in the butt.

Duplicate your rig. Pose it. Apply as rest pose (ctrl A menu). Deal with your constraints however you need to, depending on your constraints. Parent the heels to the armature, with whatever weights you want.

Then, restore the armature to its old pose. This can be by eye, or by copying transforms, bone by bone, world->world, from your original. Now, you can apply the armature modifier to your heels, and then parent them to the original armature.