@chainchomp2  
Ah okay. Thank you for the explanation.

@mjangelvortex  
This was his outfit for the harvest parade that took place within the S3 episode “One Bad Apple”, where others also costumed as various crops including carrots and grapes, or as a leprechaun. Costuming him as a pear may have been a nod to the DW fanbase but it’s really not that deep, or at least wasn’t at the time.
 
Aside, this was actually my first full-body pony vector I ever attempted; in its current form on the booru and the source it’s a revamped version that was done somewhere between a few months to a year after. The first export 6 years ago to the day looked, er, like this.

Best costume ever

@LaptonSpark  
Ah. That makes sense. Dress up as the thing he dislikes for Nightmare Night.

@mjangelvortex  

 
Maybe its his Halloween costume

I thought he hated pears.