Home » Theme Costumes » Stereotype Costumes » Cross-Dresser Costumes » Coolest Jessie from Pokemon Team Rocket Costume

Coolest Jessie from Pokemon Team Rocket Costume

Prepared for Trouble, that’s what I did…
And made it double, having fun with the kids.
Halloween 2006 and time to trick or treat;
A Jessie from Pokemon Team Rocket costume idea that was really neat!

Dressed up for laughs as a villainous lass,
Just there for All Hallows Eve and having some laughs.
I cropped off a “R”- ironed on turtleneck shirt,
And pairing it off with a scooter skirt.

Adding a flesh-colored overshirt with black gloves, boots and undershirt,
I knew the a purple wig would also have it well to work.
More like a nasty lady I gave out candy,
And the kids loved it a lot, ’twas pretty handy.

Jessie! Indeed, but I didn’t want to be blamed…

Team Rocket, having fun without having to be mean;
Having fun celebrating October 31, all on Halloween!

Coolest Homemade Costume Contest 2023

9 thoughts on “Coolest Jessie from Pokemon Team Rocket Costume”

  1. That IS a purple wig, I couldn’t get any magenta wigs at that time and yes it is Jessie we’re doing here. I retired that outfit in 2009 for a more professional costume that I wear these days.

  2. Okay everyone. Shut. the hell up. This guy is the most amazing Jessie out there cuz he had the courage to dress up as her and walk around with a huge smile on his face, and having fun while he new that he was being teased by some, praised by others. This guy was amazingly nice to my sister as ash. And I loved the picture moments. He is the most amazing Jessie you guys will ever see!

  3. I think I’ve met him before… at Zenkaicon one year. My friend and her boyfriend were dressed as Team Magma Members, and they all talked while someone cosplaying as a news reporter and her cameraman ‘filmed’ them. :) It was a certainly memorable experience, and I hope that when I’m older, I’m as cool as this Jessie is! :D


Leave a Comment