From Bulbapedia, the community-driven Pokémon encyclopedia.
Ash's hat (Japanese: サトシのぼうし Satoshi's hat) is an item of clothing that Ash Ketchum is seldom seen without. Throughout the Pokémon anime, Ash has worn six different hats so far, one for each of the six different series.
All of Ash's hats have been produced for people to wear. Ash's Advanced Generation hat was available to purchase at PokémonCenter.com before it shut down. His hats can be found at numerous stores (including the Pokémon Centers in Japan) and on online auction sites such as eBay.
Pokémon League Expo hat
Ash wearing his Pokémon League Expo hat backwards
Ash's first hat, worn during the original series, is easily the most well-known: an official Pokémon League Expo hat that was red and white with a green, stylized "L" on the front, which Ash claimed to have "sent in about a million postcards" in order to obtain. Misty seems to have tried to win it as well, as she stated she sent in one postcard. Ash wore this hat during his journey through Kanto, the Orange Archipelago, and Johto, and was very attached to it, becoming enraged when a Mankey stole it and played keep-away with it in Primeape Goes Bananas. The design may be loosely based on Red's Generation I hat, and in early concept sketches for the anime, Ash's hat matched Red's exactly.
Commonly, Ash would turn the cap backwards, particularly when he was concentrating heavily, such as when he would face a Trainer or capture a Pokémon. This was seen most often early in his journey in Kanto, gradually becoming less frequent until his journey in Johto ended, by which time he hardly ever turned his cap. The sequence was actually a common animation practice used frequently to cut costs at the time.
Advanced Generation hat
Ash wearing his second hat backwards
After returning from Johto, Ash was given a change of clothes by his mother, and he immediately changed into them, including switching his old hat for a new black-and-red one which had a green Poké Ball symbol/logo on it. He seemed to have no hesitation in changing hats, despite the attachment shown in Primeape Goes Bananas.
Like the first one, his second hat was also stolen by a monkey-like Pokémon which Ash later captured, this time an Aipom in Slaking Kong!. Unlike previous occasions, Ash actually accepted that it was gone (or so he assumed), saying that he would "feel strange" without it. At the end of the episode, Aipom returned Ash's hat to him. However, Aipom followed Ash and his friends to the Kanto Grand Festival where it stole his hat again. After Ash captured her, Aipom stole Ash's hat multiple more times as the Advanced Generation series ended and the Diamond & Pearl series began.
Ash rarely flipped his hat during the series. Occasions on which he flipped his hat include when he was dressed as an eggplant in Claydol Big and Tall, when he was cleaning the dojo in Pasta La Vista!, while sleeping with his Pokémon in Gathering the Gang of Four!, and during the climax of the ninth Pokémon movie.
Diamond & Pearl hat
Ash wearing his third hat backwards
Ash had received his third hat in a package from his mother while in the Sinnoh region. Though his clothes changed quite a bit between their Advanced Generation and Diamond & Pearl iterations, his hat remained similar; though while his second hat had a green Poké Ball symbol, his third one was blue. This hat also had a larger and square black area around the Poké Ball, while the black area in the Advanced Generation series was round.
Ash flipped this hat only twice: in his battle against Tobias in The Semi-Final Frontier! and briefly in the thirteenth Pokémon movie.
Best Wishes hat
Ash wearing his fourth hat backwards
In the Best Wishes series, Ash wore a red and off-white hat. Unlike the hats seen during the Advanced Generation and Diamond & Pearl series, this hat bore a slight resemblance to the one seen in the original series, but with a blue Poké Ball design for a logo and no line running down the middle. The hat resembles the hat worn by Hilbert from Pokémon Black and White.
In Dancing With the Ducklett Trio!, Ash's hat was stolen once again, this time by a trio of Ducklett.
During the early episodes of the Best Wishes series, Ash flipped his hat somewhat often, with decreasing frequency as the series went on. This is the same pattern seen in the original series with the Pokémon League Expo hat.
In Team Plasma and the Awakening Ceremony!, Ash flipped his hat before moving forward to help his Pokémon dig through the cave wall.
A comparison of the similarities between Ash's hat from the original series (left) to the Best Wishes
Ash wearing his fifth hat backwards
In the XY series, Ash wears a red hat with a white brim and a white semicircle across the front. This hat resembles the hat worn by Red in the games from Pokémon FireRed and LeafGreen to Pokémon Black 2 and White 2.
Ash has flipped his hat five times in this series, when he tried to catch Fletchling in A Battle of Aerial Mobility!, when he climbed the rock wall in the Cyllage Gym in Climbing the Walls!, when he searched for berries in Under the Pledging Tree!, during the eighteenth Pokémon movie and in The Synchronicity Test!. Ash has also had the tendency of adjusting his hat a lot in this series; this has been seen more commonly than seeing him flipping his hat backwards. This tendency to adjust his hat echoes Red's sprite animations from Pokémon HeartGold and SoulSilver onwards.
Sun & Moon hat
In the Sun & Moon series, Ash wears a red hat with a white Poké Ball symbol on it. The hat resembles Sun's hat from Pokémon Sun and Moon, but is red instead of black while the brim is recolored from black to white.
In the upcoming twentieth movie, Ash is shown wearing a hat resembling a blend between his League Expo hat and his Sun & Moon hat.
In the games
Six forms of Pikachu, each wearing one of Ash's six hats, will be distributed to moviegoers who pre-order tickets to the 20th Pokémon movie.
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Ash's hat in Hey You, Pikachu
In Hey You, Pikachu!, the original hat, along with the rest of the outfit, can be seen hanging on a coatrack in the player's bedroom. Pikachu uses the hat in "The Piñata Game" to cover his eyes.
Concept art of the Pokémon League Expo hat
- Early concept art of the Pokémon League Expo hat shows similarities with Red's hat in his original design from Pokémon Red and Green.