Wow, I thought it was very obvious but I guess people just don't see these things. Whomever this pony is (I can't remember his name) is trans and (as evidenced by the image of him wearing a skirt) dresses up in female clothing to feel closer to her true gender.
snips, and that would've been my second guess but that line on the torso and the smaller images made me think of someone inside
now I wish that the black and white drawings were in color so I could tell what was going on, because at first I thought they had a boner in the suit or something :X