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Maybe their thin and soft, like ballet slippers? Better for tickling through…
This is why I’m sure, that the headcanon is not workable. And he said it before Twilight becoming alicorn.
Then why doesn’t Twilight wear the shoes on a daily basis like Tia and Luna?
I heard from my friend his headcanon, that after becoming alicorn, princesses obtain high sensitiveness, so they had to walk in the horse shoes all the time. I wasn’t thinking so, but would like to believe.
Edited
That seems more likely.
Or she did something to the shoes directly.
Or perhaps they’re really super-soft-soled shoes, flimsier than a pair of ballet slippers?
Celestia must’ve done something to that feather to make it work with her shoes on.
Maybe, she is too sensetive, so without them a little breeze would be a problem for her?