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Background Pony #B721
Did they seriously imply she has been carrying Boulder around in her hooves this whole time? Forget the pocket scene, how does she walk?
Background Pony #6350
Do you have any idea how lumpy and uncomfortable that must be? For both of them?
 
Plua she just wants to spoil him with some luxury. She didn’t say he NEEDS the bag…
Evowizard25

Maybe most of her dresses just don’t have pockets. Also, never trust a shirt pocket unless it has a button. HOnestly, a pouch does fit better.
MezzoDragon
The End wasn't The End - Found a new home after the great exodus of 2012

Pathetic Failure
@DoomPony  
It depends on the cartoon. Some have characters wear completely different clothes. Others have a character wear the same thing throughout the entire series. I think MLP might be the latter. If so, then this flock may be the same one as she wore in her debut episode.
MezzoDragon
The End wasn't The End - Found a new home after the great exodus of 2012

Pathetic Failure
Actually, now that I think about it, Maud probably knows about Pinkie’s “secret” plan. Or this is just dialogue to create “tension”.
Background Pony #1DF3
It’s like when you buy a purse to someone,people.Sure,he/she can keep her junk in his/her pocket but a purse is more pratical and more truthworthy and big than your pocket
Background Pony #26EA
If this had happened in a IDW comic certain people would have screamed that it proves that IDW isn’t canon and doesn’t care about the show.  
Bias, bias everywhere
Background Pony #0FEB
Pockets suck if objects aren’t snug fit. Plus there is the issue of leaving things in pockets when you change clothes.
Lyakar

Honestly, from my experience, pockets are not the most trustworthy place to hold things. It’s fairly easy to lose things from them.  
Or maybe all of my pockets have just sucked that much.