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safe2197591 artist:sevenpaperplates39 twilight sparkle361073 pony1628007 unicorn549591 g42053392 clothes644666 clothes falling off36 female1828943 glowing19877 glowing horn29540 horn203650 human to pony2031 jeans6777 magic97929 male to female2166 mare758041 mid-transformation874 pants22923 rule 6333849 shirt41629 shoes60812 sneakers6560 tongue out149718 transformation16336 transgender transformation2726

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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.