Ash's hat
From Bulbapedia, the community-driven Pokémon encyclopedia.
Ash's hat (Japanese: サトシのぼうし Satoshi's hat) is the most important and famous item of clothing that Ash Ketchum is seldom seen without. Throughout the Pokémon anime, Ash has worn three different hats so far, one each for the three different series.
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Pokémon League Expo hat
Ash's first hat was easily the most well-known of them: an official Pokémon League Expo hat that was red and white with a green "L" on the front, which Ash claimed to have "sent in about a million postcards" in order to obtain it. Misty seems to have tried to win it too, as she stated she sent in a postcard too. Ash wore this hat throughout all of 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.
Commonly, Ash would turn the cap backwards, especially when he was concentrating heavily, such as when he would face a Trainer or capture a Pokémon. This was very much the case early in his journey in Kanto, though by the time his journey in Johto ended, he hardly ever turned his cap.
Advanced Generation hat
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 on it. It is assumed that he left the old hat at his home in Pallet Town, where it may still be.
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! In a surprising display of maturity, however, Ash did not climb any trees or scream at Aipom when his hat was stolen. Instead, he 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 and Pearl series began.
Diamond & Pearl hat
Ash's most recent headgear, Ash received his newest 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 astoundingly similar, though while the AG hat had a green Poké Ball symbol, the DP one was blue. The DP hat also has more black area around the Poké Ball, being square while the black area in the AG series was oval-ish.
Real world
Both Ash's original hat as well as the Advanced Generation hat have been produced for people to wear. Although, Ash's Advanced Generation hat was available to purchase at PokémonCenter.com before it shut down. The original can be found on eBay, among other auction sites, if one is lucky. Ash's Diamond and Pearl hat is currently being sold at the Pokémon Centers in Japan.
