Jessie and James have sported a ton of disguises throughout Pokémon. Sometimes the costumes are so ridiculous and goofy that they just steal the show. Also, James' cross-dressing is such a highlight. He is such a self-confident inspiration and fans love him for his many outfits.
Obviously, we cannot rank every disguise they have done so we just picked ten and are ranking them from worst to best. Of course, most of them include James cross-dressing, or else this list just wouldn't be fun. From Swan Lake outfits to dressing up as Ash and Serena, here are a ranking of ten of Team Rocket's disguises.
10 Hula Girls
These disguises were used in the Kanto season for the episode "Abra and the Psychic Showdown."
In terms of a disguise that works to hid their identity, the hula outfits are great. You wouldn't recognize James or Jessie. However, it is very strange that their skin colors have gotten darker. Did they quickly go to a tanning salon? Also, why hula? This happens in Saffron City, and honestly makes them even more noticeable in a crowd. It is not like the Aloha region where people dressed in hula outfits would be normal.
9 Ganguro Style
The meaning of this disguise was lost for most non-Japanese audiences. James and Jessie are dressed in a particular Japanese fashion called "ganguro" which is known for having dark tanned skin with bright make-up. These styles are often seen in other anime as well, but it is not typically explained for international audiences.
They dressed like this in "Battle Aboard the St. Anne" and what makes the disguise special is that it is the first time we see James cross-dress.
8 Punk Rockers
Apparently James and Jessie really liked these disguises because they reused them in three different episodes. They used them for "The Song of Jigglypuff," "A Breed Stampede!," and "Fighting Ire with Fire!"
In terms of a look, it is very 1970s and they pull it off well. Maybe it is not so much that they think the disguise works well, but they just love wearing those leather jackets and colorful wigs. However, these are one of their outfits where you can actually not recognize them. The sunglasses really help James and the hair change would certainly stump some people.
7 Pink Pokémon
Now, this is just plain cute. Jessie and James dressed like this for two episodes, "In the Pink" and "Manectric Charge."
The first time they use the costumes is due to inspiration from Pinkan Island, which is an area that is full of pink-colored Pokémon.
In terms of usefulness, it's pretty unbelievable that these disguises would work on anyone. You can see their faces in the mouths! Also, while it's adorable, it is not the most creative. In the Pokémon world, it's probably easy to obtain outfits like these.
6 Swimsuits
Oh James, you have provided us with a gift. The United States was not ready for you because we were too weak. The episode where James defies his own anatomy was initially banned in the U.S.A. because apparently men cannot be so curvy in America.
The episode was called, "Beauty and the Beach." Obviously, James stole the show. For Jessie, the swimsuit is not even a disguise. James however, he somehow changed his entire body. It is like his head was placed on a Barbie doll.
5 Egg-Sellers
In the episode "Who Gets to Keep Togepi?", James and Jessie disguise themselves as female egg-sellers. The costumes are rather strange and old fashioned, complete with bonnets, baskets, and old dresses. Somehow that is what Jessie and James pictured when they thought of egg-sellers, the Amish.
Since the bonnets and dresses cover a lot of their bodies, the disguises do hide their identities pretty well. Also bonus points for James for cross-dressing again. You go, James.
4 Pokémon Fashion
We did say "Team Rocket" disguises, and those members do not always include humans! They dressed up their Koffing and Ekans in the episode "Pokémon Fashion Flash" and they look amazing. If it was James who dressed up his Koffing, his fashion skills just stole the show again.
That Koffing is so beautiful and so happy to be wearing a tutu, flower, bow, blush, mascara, eye-shadow, and lipstick. Ekans is cute but does not have that same ridiculous charm as Koffing is sporting in this episode. What icons.
3 Ballet Dancers
These costumes were used in the episode, "The Misty Mermaid." They dress for the Cerulean Gym's Underwater Ballet show. In this same episode, Misty dresses up as a mermaid which gets a lot of fan art. However, fans still cannot forget James' tutu. Jessie takes the role of the prince and James just goes full James on us. Meowth is included too but al he has is a swan float ring.
James tutu was a big enough hit that he uses it again in the episode "Flower Power."
2 Magicians
In the episode "The Purr-fect Hero," Jessie and James put on a fake magic show for schoolchildren. Like in many of their disguises, they switched gender roles. Jessie is the magician with a top hat, glasses, and tuxedo while James is the eye-candy magicians' assistant in a cute dress.
They are pretty easy to recognize though. Any fan can recognize their hair a mile away. Still, its ranked highly on the list because of them switching gender roles. Those are always their most memorable disguises and its obvious that they are having fun doing it.
1 Ash And Serena
Team Rockets' best disguises are when they dress up as the heroes themselves with James dressing up like Ash and Jessie as the female sidekick. If you squint or see them from a distance, the disguises are very convincing. That Pikachu they have is complete and utter nightmare fuel though. If you are wondering, that is James' Inkay that they disguised as Pikachu. Yikes.
It is the best because it is the most convincing of the ten we have chosen (except for the Pikachu, we are ignoring that abomination).