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Several things define when one arc of the Pokemon anime ends and the next begins. The individual series are pretty cleanly divided by name, region, companions, and sometimes even animation style. However, it doesn't truly feel like a brand new adventure until Ash dons a brand new hat.
Ash's hat is almost as big a part of the character's iconography as Pikachu. No matter what the style of his overall outfit, the baseball cap will always sit atop his messy hair, and when he turns it backward, viewers know it's time to get serious. Each hat has its own little touches that make it great, and how they mesh with the rest of his outfit is also important.
8 Kalos Arc
Ash's outfit during his adventures in Kalos is quite clean, and that makes it a little boring. It's understandable from a character sense; this version of Ash was a lot more mature than the one from Unova, but it took away a bit too much of the character's messy edge.
The hat plays into this, and unfortunately, it clashes with Ash's outfit a bit too. All of Ash's outfits have a mixture of red and blue in them, but the rest of the outfit has so much blue that this hat's all-red design feels a bit out of place. The design is pretty dull, too, a single white arch that means absolutely nothing.
7 Unova Arc
This hat is undeniably a lot better than the Kalos one, but it feels a little too on the nose. The hats have always hinted at Pokemon imagery on them, but to go all the way and actually put the Pokeball symbol on it is a step too far.
That said, it's not a bad design. The blue and white work well together, using red to highlight the design. It meshes well with the rest of his outfit too. The Pokeball just detracts from the point of it. Ash shouldn't be wearing Pokemon merchandise...he is the Pokemon merchandise.
6 Alola Arc
The Alola hat is an evolution of the Kalos hat. That means it adopts some of the same problems, but it is a much better design as a whole. The symbol on the cap is much more interesting. The broken hexagon feels unique while still being somewhat reminiscent of the original design.
The clashing problem between the red and blue is still there but to a much lesser extent. Firstly, the rest of Ash's outfit has more white and less blue, but also the blue rim on the hat brings a lot more visual cohesion to the design.
5 Hoenn Arc
The first change of hat following the Johto arc, this hat manages to be something new while hanging on to the old. The thing is, it would've been much better leaving the old behind completely. The symbol on the hat is really nice. The two shapes used are very simple, but they're perfect for this element of the costume. They manage to invoke the idea of a Pokeball without straight-up being one.
The problem is the green; it doesn't work with the black and red held by the rest of the hat. It's understandable why this was done. The symbol on the original hat was green, but that only worked on the white background. Thankfully, people who liked this design would be pleasantly surprised when Ash moved to Sinnoh.
4 Sinnoh Arc
Much like the Alola hat evolving the Kalos hat, this hat from Sinnoh is a total improvement on the Hoenn hat. The cool symbol remains the same, only now its color has been changed to a soft blue. This works wonders with the black background, which has now been extended, pushing the red to only sit around the edges.
It helps that the rest of Ash's Sinnoh outfit is a lot more visually interesting too. Mixing white, black and yellow allows the shirt to do its own thing, while the hat brings more color to the design. This feels like the definitive version of Ash for the early years of the anime, even down to how his trousers are too long for him, and they crumple over his shoes slightly.
3 Kanto/Johto Arc
While Sinnoh may be the most refined version of Ash's outfit, there is a clear charm to what the original did. Ash's whole outfit comes together for the first two arcs of the show. His trainers are cool and understated, his jacket mixes blue and white, throwing in some yellow highlights, then there's the hat.
It's been long enough that calling it an iconic design feels like fair game. The white background frames the green Indigo League symbol perfectly, encapsulated by the red makes for such a tight design. There isn't much negative to be said about it, perhaps only the fact that the Indigo League symbol is a bit too small and leaves too much white space on the hat.
2 Journeys Arc
For a very unique arc of the anime, it's only fitting that Ash gets a unique hat. Here, Ash isn't tied down to any one region as he travels all over the world to serve his goal of becoming a Pokemon World Champion and Goh's goal of completing the Pokedex.
The red design with the white brim is a great place to start. This outfit uses blue quite sparingly throughout, so there's no clashing issue. The symbol on the top is by far the biggest, but there's a lot to like about it. Much like the customization options in Sword & Shield, it mimicks the logos of clothing brands in a way that feels unique to the franchise.
1 I Choose You!
This anime movie rebooted the Pokemon movie franchise into a new continuity, starting from Ash's very first adventures in Kanto with new friends and rivals. Naturally, they were going to need a modern take on his original outfit. Fans were understandably wary of this, but thankfully the team did a fantastic job.
Most of the outfit doesn't change much at all, the design is just cleaned up a bit from the old 90s animation style. The hat is the most noticeable change. The white background and red border are still there, framing the center of the hat nicely. What's changed is the Indigo League symbol, which is now bigger and bolder, taking up most of the white space on the hat, fixing arguably the only problem with the original hat design.