It is the day of the Lilypad Contest, and Dawn is excited to enter. Across town, Jessie is focused on winning her third Ribbon, but she is sick, so James and Meowth convince her to stay in bed. To help his friend, James disguises himself as Jessilina and takes her place.
Meanwhile, Dawn makes the decision to use Mamoswine in the battle round. Lyra expresses the gang's concern in this choice, seeing as this Contest holds the pivotal fifth Ribbon Dawn needs to enter the Grand Festival. However, Dawn feels confident in her choice.
While in the waiting room, the gang meets James in his guise as "Jessilina". Lyra makes a remark about the outfit he is wearing, and he quickly gives a response before ducking into a corner, indicating it's been a long time since he's cross-dressed. Meowth reassures him, reminding him that he's doing this for Jessie.
The first round commences, and in a quick set of moves, Dawn's Piplup uses Whirlpool and then Bide to leave a dazzling impression on the minds of the judges. "Jessilina" uses Meowth and Fury Swipes to make delicious ramen for the judges, and they are quite impressed with the showmanship and flavor of the meal. Throughout the appeals round, Brock describes to Khoury the purpose of the appeals round, as Contests are completely new to Khoury.
Backstage, Piplup appears confident and satisfied with its win. The screen lights up, and it is revealed that Dawn is moving on to the next round--along with "Jessilina". In the next round, Dawn uses Mamoswine. The Coordinator she is up against sends out a Granbull. Mamoswine proves itself powerful when Dawn commands it to use its newly found combo of swallowing Ice Shard, much to the surprise of the audience. Mamoswine gains ice spikes along its back, which it then couples with Hidden Power and Take Down for a quick one-hit knockout of the Granbull. This shocks Dawn, and she reveals backstage that she had been hoping to test more of Mamoswine's combos before the match was through. Ash and Brock attempt to cheer her up, and help her to be happy that she's going on to the next round.
As the rounds progress, James uses Carnivine to great success, moving on up in the tournament. Throughout the battle round, Brock explains to Khoury the mechanics of what goes on.
It comes down to the semi-final match, and James finds himself up against Dawn. He sends out Carnivine (who naturally chomps on James's head at first) and Dawn sends out Mamoswine. Dawn starts off the match with an Ice Shard, but to her surprise, "Jessilina" is prepared and has Carnivine use Vine Whip to steal the Ice Shard before Mamoswine can eat it. This startles Mamoswine causing it to start to get worked up while Carnivine playfully juggles the Ice Shard. Meowth, sitting backstage, notes to himself that James could possibly win the match. Carnivine returns the Ice Shard back towards Mamoswine and, as Mamoswine is still in shock, it does not react in time to dodge and the Ice Shard hits it square on the head costing Dawn some points. Mamoswine begins to become enraged, and Dawn tells her Pokémon to calm down but instead Mamoswine charges and (without being commanded) uses Take Down in an attempt to hit Carnivine. Carnivine proves itself too agile for Mamoswine, and dodges by simply leaping over the Twin Tusk Pokémon. Mamoswine runs backwards and forwards trying to hit Carnivine only to miss everytime and the constant failed attacks causes Dawn's points to quickly drain, while Dawn frantically tries to bring Mamoswine (who is becoming even angrier) under control.
After a couple of more failed attempts at Take Down, Mamoswine then tries to use Hidden Power against Carnivine however James has it use Bullet Seed which counters Hidden Power. Mamoswine then fires AncientPower, but Carnivine spins elegantly out of the way causing Dawn to lose more of the few points she has left. Mamoswine once charges Carnivine, who James then orders to use Vine Whip and snags Mamoswine's tusks to its surprise. Carnivine then yanks back hard, throwing Mamoswine forward off its feet, which combined with its charging forward momentum, sends it violently sliding on its chin across the stage towards the judges! It quickly becomes clear that Mamoswine won't be able to stop in time, and Mr. Contesta, Mr. Sukizo and Nurse Joy barely scramble out of the way just before Mamoswine's body is halted by crashing into and destroying the judges boxes. Dawn runs forward worried that Mamoswine has been seriously hurt, but Mamoswine tries to get up clearly ready for more.
With that, time expires, and it's no surprise to anyone that "Jessilina" has the most points remaining. Mamoswine has calmed down, but is clearly saddened as it already knows that its behavior has cost Dawn her Contest. Dawn tries to cheer Mamoswine up, saying they'll do better next time.
Later, it is revealed that "Jessilina" has won the Lilypad Contest, and James proudly shows off his Ribbon alongside Carnivine and Meowth. Jessie sees this on television and is thrilled, though when James comes by later to give her the Ribbon, she is upset because the audience liked James better as Jessilina than they liked her as Jessilina. James and Meowth just shrug; Jessie will be Jessie.
That evening, Ash, Brock, Dawn, Lyra and Khoury leave Lilypad to their next destination. Dawn gives Poffins to her Mamoswine for its efforts and while sorry she lost the Contest, pledges to win the next one, earn her final Ribbon, and go to the Grand Festival. Next time, she'll be ready.
- 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.
- This marks the first time Dawn's whole team did not cheer for her in a Contest.
- 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.
- This is the only episode of the Lyra and Khoury arc in which Khoury's Totodile does not appear.
- One of Hitmontop's feet is miscolored.
- In the Brazilian translation, Piplup's Bide is mistranslated as "Bite".
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