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safe2268700 artist:sevenpaperplates40 twilight sparkle371473 pony1701345 unicorn582141 g42127600 clothes678911 clothes falling off38 female1910362 glowing22735 glowing horn31138 horn242641 human to pony2437 jeans7271 magic101963 male to female2250 mare806881 mid-transformation1041 pants24993 rule 6334827 shirt45082 shoes65433 sneakers6787 tongue out157112 transformation17631 transgender transformation2954

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Background Pony #E0C6
@OneAmongOthers  
Probably most of it is size changing, changes in proportions, and for everything else the person in question intentionally taking it off through tactical squirming and shuffling.
 
As it happens human clothing fits humans very well on humans and in most cases it doesn’t fall off very easily. We have yet to understand how or why this happens, but we understand the phenomena well enough to understand that it doesn’t transfer to horse very well.