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Champions of Equestria

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Description

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safe2279481 artist:sevenpaperplates40 twilight sparkle371392 pony1709292 unicorn586619 g42122066 clothes678409 clothes falling off38 female1910200 glowing23246 glowing horn31435 horn250385 human to pony2633 jeans7224 magic102856 male to female2316 mare812999 mid-transformation1141 pants25029 rule 6334985 shirt44995 shoes65875 sneakers6803 tongue out156739 transformation18176 transgender transformation3055

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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.