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safe2248178 artist:sevenpaperplates39 twilight sparkle368711 pony1679229 unicorn572053 g42108870 clothes668448 clothes falling off38 female1887177 glowing21889 glowing horn30673 horn230616 human to pony2130 jeans7148 magic100673 male to female2219 mare792307 mid-transformation923 pants24571 rule 6334543 shirt44143 shoes64118 sneakers6715 tongue out154969 transformation16911 transgender transformation2810

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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.