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safe2211983 artist:sevenpaperplates39 twilight sparkle363183 pony1642144 unicorn556520 g42066514 clothes651351 clothes falling off36 female1846185 glowing20470 glowing horn29884 horn211984 human to pony2067 jeans6898 magic98750 male to female2198 mare768459 mid-transformation893 pants23205 rule 6334159 shirt42429 shoes61590 sneakers6604 tongue out151241 transformation16531 transgender transformation2759

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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.