Ash Ketchum of Pokemon anime fame has had his fair share of outfits over the years. What’s stood out on most of them were his choices of headwear. If there’s any character out there in any franchise that’s known for his hats, it’s the ever-so-loose cannon himself, Ashy-boy.
No, not all of them were slam dunks. Aside from the main outfits that he cycles through with the seasons, he’s also had a few offshoot outfits and headwear from certain episodes and even movies, and some of them are a little freaky. This list with take a look at most, if not all, of his headwear choices over the years, all the way from grossly grotesque to ridiculously rad.
17 Ashley Wig
Knowing how Ash’s hair actually looks like, seeing Ash with fake Goldilocks-blonde hair can range from awkward to vomit-inducing. Crossdressing isn’t necessarily bad, but the fact that he wore the Ashley wig the first time as a ploy to enter the Celadon City Gym unconsented is problematic beyond belief.
16 Army Hat
Ash wore this hat for a few episodes of the Original Series, along with a standard Army outfit. No matter how good it would potentially look in real life, the basic cross-hatch pattern drawn onto the hat is just hideous. At least Misty wore a beret.
15 Hearthome Collection Wig
Why Ash went with this kind of caveman-like costume for a fashion show is a bit head-scratching, but at least it won an award for the most original costume, or something. At the very least, the nice shade of blue on the wig helps it stand out.
14 Mewtwo Strikes Back Evolution Hat
While the rest of Mewtwo Strikes Back—Evolution’s visuals could be considered as potent nightmare fuel, at least the hat looks OK when rendered to 3D.
13 Wallace Cup Costume Fedora
It’s not much. It’s just a fedora. At the very least, its simplicity puts a nice finishing touch on his outfit for the Wallace Cup, which otherwise looks kinda janky with the unnecessary amount of frills on the jacket.
12 Diamond & Pearl Main Hat
While you’d expect blue to work better with red most of the time (see: his XY outfit), the way it was pulled off on his Diamond and Pearl hat was kinda dull. The wider black stripe makes it look just a little less slick than his Advanced Generation hat. Still, it’s somewhat of a bright spot on an otherwise awkwardly put-together outfit.
11 Advanced Generation Main Hat
It’s a decent hat in conjunction with the rest of Ash’s colorful Hoenn outfit, but it’d be pretty difficult to wear it on any other outfit without making it look jarring. Red, black, and green on a hat would look weird in any other context. At the very least, the little details on it are a bit better than those on his Sinnoh hat.
10 Alternate Timeline Main Hat
It’s essentially a rehash of Ash’s most popular hat, but it’s a bit inferior. The rounder shape and reworked green symbol at the front might look weird if you’re familiar with the original.
9 Black & White Main Hat
Compared to his main hats from the previous two seasons of the anime, this one was a bit of a change-up. The stark red, white, and blue colorway is a pretty interesting design choice. If only it didn’t give Pokemon fans war flashbacks of Ash’s stupidity and complete battling incompetence from the consensus-worst season of the anime.
8 Movie Knight Costume Hat
Ash wore this whole fit for his role as a knight in a movie. While the entire outfit looks pretty darn cool mixing medieval and futuristic elements, the hat is a bit underwhelming being just a plain blue. It, coincidentally, looks like a ripoff of his hat from the eighth Pokemon movie.
7 Volcanion And The Mechanical Marvel Beret
Ash wore this outfit through quite a bit of the 19th movie’s runtime, and while it’s a bit confused on whether it wants to be modern or old-school, the beret with the Poke Ball symbol hanging on the side is pretty slick.
6 Original Series Main Hat
The OG is iconic as can be; the green L-shape on the red and white hat has become one of the Pokemon franchise’s instantly-recognizable symbols.
It would probably look pretty repulsive without the association to the Original Series, but the nostalgia just speaks to a lot of people when looking at this hat. Hey, that’s just how the cookie crumbles.
5 Journeys Main Hat
Ash’s newest main hat is a bit similar to his Hoenn hat in that it goes for a look with both red and green, but it pulls it off much better.
It has a very unique symbol on the front: a Poke Ball that also seems to resemble a PokeDex. It stands out in its own way without taking too much of the spotlight from the rest of his Journeys outfit, which is all you can really ask for.
4 Pokemon Musical Costume Top Hat
Like his Wallace Cup fedora, this tall red top hat works great with the rest of this glistening red tuxedo fit that Ash wore for a Pokemon Musical. All things considered though, it’s a good-looking top hat. He could even look like a charismatic circus ringmaster given the right outfit.
3 Sun & Moon Main Hat
Ash’s Sun and Moon outfit is one of his more laidback ones, and the same goes for the hat. Red with a little bit of white would look nice on most fits, and the somewhat minimalist rendition of the Poke Ball symbol makes it pop just enough. He also finally won a League in this hat, so maybe all of his other hats carry some sort of curse that this one doesn’t have.
2 XY Main Hat
Simple and sharp. Another red and white color scheme, but this one’s a little better. It’s enough of a deviation from Ash’s other hats without straying too far. It works excellently with the rest of the blue-dominant outfit, which is at least 60% of the reason why XY Ash was so effortlessly cool, considering its connection to the Ash-Greninja form and all. As it stands, Ash’s XY hat is his best main series hat.
1 Lucario And The Mystery Of Mew Hat
It’s surprising that this Sir Aaron-inspired outfit isn’t talked about as much considering Ash’s aural connection to Lucario, because it’s a wicked good costume. This whole fit from the eighth Pokemon movie perfectly blends vigor with elegance. The hat is an excellent finishing touch, with the yellow half Poke Ball paying homage to his main hats. If he’d kept the hat as a reminder, he might’ve gotten a Lucario sooner.
NEXT: 10 Hilarious Ash Ketchum Pokemon Memes That Are Too Funny
