She sure does! We need more images of Pinkie Pie and the other female characters wearing barrels.

I think that Pinkie looks good wearing a barrel

Gilligan’s

It looks like they are all in a standing position.

@cdcdrr  
Great theory, but as this picture was asked for by me I can tell you the real story. These are AU versions of the characters from my upcoming fanfic “Equestria Girls N’ Goblins” where Pinkie Pie, Rainbow Dash and Fluttershy are knights in a world like in the Ghosts N’ Goblins and Ghouls N’ Ghosts video games by Capcom. While on a quest they fought a bunch of monsters which resulted in them losing their armor and ending up in their underwear, something the GNG games are famous for. Fluttershy opened a treasure chest hoping to find some armor in it but instead found Trixie the witch who quickly cast spells on them transforming them into more helpless forms. Pinkie Pie lost her weapon and had her underwear replaced by a barrel, Rainbow Dash was turned into a mermaid who can still fight but can’t move well on land and Fluttershy had her underwear turned into a leaf bikini and her weapon turned into a plain stick.”

Dash is dressed as the little mermaid, Fluttershy is ‘dressed’ as Eve, and Pinkie Pie as someone who lost a lot of money at poker.

This Reminds Me A Whole Lot OF Gilikins Island