Before the Contest, Ash and Dawn train. Grotle uses Energy Ball and Mamoswine Ice Shard, but they swallow them. Brock explains to Khoury and Lyra that when Grotle swallowed Energy Ball by accident, Dawn and Ash now learned how to power their Pokémon up. Since it worked, Dawn now sees that she has a chance to win. Cyndaquil lets fire out its back to prove it can be in a Contest, but Dawn disagrees; she has Piplup and Mamoswine to compete in this Contest. Still, she lets it cheer for them and when she hugs it, Piplup gets shocked and Dawn burned by Cyndaquil. Nevertheless, she promises to get the last Ribbon.
Meanwhile, Jessie got stck, but still wants to compete in the Contest. James and Meowth stop her and tell her she needs to let this one go. Jessie does not want to, but has a back-up plan. The Contest is about to begin, so Lyra, Brock, Ash and Khoury visit Dawn. Lyra remarks Dawn's dress and sees that her confidence is nearly as big as Ash's confidence. She sees another Coordinator and Ash, Brock and Dawn recognize her as Jessilina. Lyra remarks her dress and asks where she got it, but she does not know and nervously goes out. It is James who is dressed like her and doubts he will win, though Meowth reminds him he needs to or Jessie will be sick even more.
First is Dawn, who sends Piplup. He starts using Whirlpool and uses Bide before engulfing himself in the Whirlpool, glowing by a blue light. Lyra and Khoury agree that the first round can be called as a Talent Show. After some performances, it is James (aka Jessilina)'s turn. He sends Meowth (without using the Poké Ball), who uses Fury Swipes to cut a noodle ball to get some noodles (making Christopher proud). Lyra is proud of Piplup's performance, even James thinks he can get into another Contest. The judges decided the eight Coordinators; among them are Dawn and Jessilina. Now, Dawn has decided to use Mamoswine, even if Lyra thinks Buneary is a better choice.
Dawn sends Mamoswine and her opponent a Granbull. Granbull starts with Fire Fang, though Mamoswine dodges. Mamoswine uses Ice Shard and swallows it. Mamoswine uses Hidden Power and circles around itself, then takes down Granbull. This causes Granbull to be defeated, so Dawn wins, even if she is surprised how little it took her. Dawn feels a bit sad, as she could have displayed Mamoswine even more. Nevertheless, she decides to display Mamoswine a bit more in the next round. After some battles, James and Dawn got into next round. Dawn sends Mamoswine and James his Carnivine.
Mamoswine uses Ice Shard and goes to swallow it, but Carnivine snatches it using Vine Whip. Being all furious, Mamoswine fails to dodge Ice Shard Carnivine returned. Mamoswine is very angry and uses Take Down without Dawn's orders, though Carnivine jumps to dodge. Mamoswine goes to take down Carnivine, but misses. It uses Hidden Power, but misses, as Carnivine even dodges AncientPower. Ignoring Dawn's orders, Mamoswine goes for another Take Down, but Carnivine uses Vine Whip to bind its tusks and send it down. This causes the judges' table to be destroyed and time is up. With all the order ignorance, Mamoswine gave Dawn a loss and Jessilina a victory.
Mamoswine is sad, even if Dawn tells it there is next time to win. Lyra tells Dawn she should have used another Pokémon instead, but Dawn is not worried, as she had to see what Mamoswine offered. Lyra is surprised that Dawn is so positive. Suddenly, they hear Jessilina won the last battle and the Ribbon. Team Rocket is happy that James got the Ribbon. While pleased, Jessie is angry that James and Meowth got a lot of applause. So, she puts her dress on (as she is cured) and promises to get more Ribbons, making James and Meowth relieved they are not scolded. Dawn gives Mamoswine some Poffins and promises to train even harder, while Brock and Ash offer help to get her the last Ribbon.
- With the exception of those owned by main characters, all of the Pokémon that are seen to be entered in the Lilypad Contest were introduced in Generation II.
- Instead of Professor Oak's lecture, a preview of the Team Galactic finale was shown, which was revealed to be airing in November 2009 in Japan.
- This is the first episode since One Team, Two Team, Red Team, Blue Team! to have Piplup returned to his Poké Ball for a period of time.
- James's win of the Lilypad Contest marks the first time a main character participated in a Pokémon Contest and won it on their first try.
- In addition, it also marks the first time James has cross-dressed in the Diamond & Pearl series, something that used to be a frequent running gag for him.
- This episode's English title is most likely based on the phrase dressed for success.
- Similar to Where No Togepi Has Gone Before!, no dub added music was present within the episode, including the title card music.
- During Dawn's appeal round, an instrumental version of By Your Side ~Hikari's Theme~ is used.
- One of Hitmontop's feet is miscolored.
- In the Brazilian translation, Piplup's Bide is mistranslated as "Bite".