The Pokémon series has remained around the same over the last twenty years it has been on TV, but subtle variations have always been present every few years when a new season comes about and Ash sets off in a fresh adventure.

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During these times of transition, Ash has taken to donning new clothes to signal the arrival of a different location, with some of his choice of garments becoming iconic in pop culture; some others haven’t left much of a mark. With the latest series once more bringing in a new get-up for Ash, we’re looking back at the five best and the five not-so-great looks Ash has had over the years.

10 Worst: Team Rocket Attire

Ash wearing Team Rocket's uniform Pokemon

During one of the seemingly thousands of run-ins Ash has had with Team Rocket during the last two decades, he and his friends decided to give Team Rocket some of their own medicine by donning their get-ups, much to their chagrin.

It’s a good thing this was only a temporary set-up, though, because Ash looked like some kind of wannabe who wanted to impress Team Rocket rather than antagonize them. The tight-fitting robes just don’t match with Ash’s short frame, although even Brock couldn’t pull the look off either.

9 Best: Advanced Generation Attire

The donning of this look was the first time in the series that we had seen Ash adopt a different outfit, and thankfully it was a good choice as Ash sure did look the part for the “Advanced” aspect of the series.

A darker scheme with the addition of a hoodie signaled Ash toward bigger things to come, and the crescent of the bottom of a Poké Ball on the pocket of the hoodie was a nice touch to add in an air of expertise toward Ash’s character.

8 Worst: Diamond & Pearl Attire

Ash Ketchum plays with his Pokemon.

There was no imagination that went into this costume, as the clothing style looked like Ash’s original one just with the jacket buttoned up and a weird yellow streak running through it. If an empty look had an image, this would be it.

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With the series also having taken another direction, this wasn’t the time to dial it back on the flashiness in Ash’s design, since this look made it seem as if Ash wasn’t really going on much of an adventure and was dressed too casually.

7 Best: Competition Attire

Ash Ketchum pointing ahead in Pokemon.

Ash donned this look when he was in a competition against May and Dawn, and it was a good decision to make him look the part of someone who wanted to compete in a show rather than a battle.

It was the right choice to avoid an actual suit and go with a look that had Ash come across like a mysterious traveler who could surprise you with his distinct style. The full white gloves and the hat also had him appear older than he was, which was a welcome change.

6 Worst: Traditional Attire

Ash has always been more of a modern kid than someone who goes traditional, and all his exploits are fun because he looks to break barriers and avoid conformity. Maybe for this reason, he doesn’t look that great in traditional garb.

This is a kind of costume choice that goes better with the female characters, or perhaps someone like Brock who isn’t aggressive with his personality. The traditional style just seemed too temporary to be taken seriously.

5 Best: Best Wishes! Attire

The coziest costume prize would be given to the Best Wishes! outfit Ash had on during the series, as he looked particularly snug during this point in time. The change from darker to lighter colors was a nice change from the usual norm before this.

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Ash also looked more his age, which was good mainly because he’d been on the show for so long you’d have forgotten he was supposed to be 10-years-old. This time, he wore a proper hoodie, one that looks good enough to purchase in real life too.

4 Worst: Mystery Of Mew Attire

In what has been considered as the best movie in the series so far, Ash and his friends were dressed up at one point like people from the king’s court, with all of them coming across more like court jesters than having a royal image.

While Pikachu looked cute as a button at this time due to his chubby and short appearance, Ash really wasn’t pulling it off, looking like a rip-off of the legend of Zorro than someone in for an adventure.

3 Best: XY Series Attire

The attire in this series resembled greatly the one we’d seen in the Advanced days, with the notable difference of the cap which carried the crescent of a Poké Ball. It was a slick look that had Ash be a straight-to-business type of person.

The shorter jacket, baggier trousers, and darker boots all came together to make Ash seem like a total pro this late in the series. In scenes that had Ash be totally serious, the costume greatly amplified the sentiment he was meant to carry.

2 Worst: Sun & Moon Attire

For some reason, the show decided on making the presentation of the animation look completely cartoonish a few years back, and Ash’s look has greatly suffered since then. Here, he came across looking much younger than he ever was.

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It didn’t help that the outfit he donned looked like something a novice would wear, as gone were the cool hoodies and jackets he once wore which were now replaced with a simple striped shirt and a hat that didn’t even have a full Poké Ball on it.

1 Best: Original Series Attire

Ash Ketchum next to Pikachu in Pokemon

It’s been over twenty years since we first saw Ash in this get-up, and there’s still no costume that has been able to usurp the mark this one left on us. Back in the day, it made Ash look like the hippest and coolest character there was on TV.

The mini-jacket, along with the contrasting colors of black and white underneath it have been duplicated by hundreds of cosplayers out there, and this is still the quintessential Ash outfit that fans most identify with. All in all, the original series attire has stood the test of time and we wouldn’t mind if it returned at some point.

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