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The earliest I know of is probably the Curious Oysters from the 1951 Alice in Wonderland Disney film.
But I would also like to know the earliest instance of a shaggy dog with no visible legs wearing something on their, y’know, “invisible paws”, like this one of Dougal from The Magic Roundabout wearing boots despite having no visible legs (dated 1968): https://www.ebay.co.uk/itm/186335520081?itmprp=cksum%3A1863355200816dab1c06308142e19ba16459201327f3%7Cenc%3AAQAJAAABcLSVkHmTL63bebovD9RfpraPWbY9f4anjbziTIaEIOVXg2DWhVLks3Lfqff9vxxfjIh4XEXusIehlT2iEH8%252BCxXNySMxlDIQJ3g86%252Bx3AAIAq9gznqdGSR72ksP41kjzPN1reUbVsJuld0S4i4qXlQfTmkMeIJTCXTM8mLpr7ju2fMvruDu87ZX%252B4bShOvD%252B4jEY06Ug5SGEFGmCYhuAEgRbr4UPW5xAIlQQLmZnhQt3XlOX%252FSaSLVeveQXVL0znyMW%252BJ6QpOoxh7evlHYQMKXyNXOPGgCSYn%252FtQAUundhKW5utUwyWJ5CF1OLteCus6dQvFcGW3oaDBt2%252FIIOUCXwMRuSQCmq%252BQgFurupr8koBa10DOs%252BTQqfVKJ8rsZzEUZXJholHO3OcD%252FFnzeHfrIQhEPrr61%252BTzjauEM4xHQ06WJ3bM9LPfkbWV%252Bw9RTRsUTrz7zRvdZ4KPqr5C1YyTs53o9pt20ZMTgvMICC72cDJ6%7Campid%3APL_CLK%7Cclp%3A4429486&itmmeta=01HSPZC5WVY0NW69NH8MAN4XZG (the 5th image)
And this one where he wears horseshoes even though his paws aren’t shown (dated 1974): https://comicvine.gamespot.com/playhour-1033/4000-772707/
I apologize if this comes off as weird in any way, I just find it cute for some reason.
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The earliest I know of is probably the Curious Oysters from the 1951 Alice in Wonderland Disney film.
But I would also like to know the earliest instance of a shaggy dog with no visible legs wearing something on their, y’know, “invisible paws”, like this one of Dougal from The Magic Roundabout wearing boots despite having no visible legs (dated 1968): https://www.ebay.co.uk/itm/186335520081?itmprp=cksum%3A1863355200816dab1c06308142e19ba16459201327f3%7Cenc%3AAQAJAAABcLSVkHmTL63bebovD9RfpraPWbY9f4anjbziTIaEIOVXg2DWhVLks3Lfqff9vxxfjIh4XEXusIehlT2iEH8%252BCxXNySMxlDIQJ3g86%252Bx3AAIAq9gznqdGSR72ksP41kjzPN1reUbVsJuld0S4i4qXlQfTmkMeIJTCXTM8mLpr7ju2fMvruDu87ZX%252B4bShOvD%252B4jEY06Ug5SGEFGmCYhuAEgRbr4UPW5xAIlQQLmZnhQt3XlOX%252FSaSLVeveQXVL0znyMW%252BJ6QpOoxh7evlHYQMKXyNXOPGgCSYn%252FtQAUundhKW5utUwyWJ5CF1OLteCus6dQvFcGW3oaDBt2%252FIIOUCXwMRuSQCmq%252BQgFurupr8koBa10DOs%252BTQqfVKJ8rsZzEUZXJholHO3OcD%252FFnzeHfrIQhEPrr61%252BTzjauEM4xHQ06WJ3bM9LPfkbWV%252Bw9RTRsUTrz7zRvdZ4KPqr5C1YyTs53o9pt20ZMTgvMICC72cDJ6%7Campid%3APL_CLK%7Cclp%3A4429486&itmmeta=01HSPZC5WVY0NW69NH8MAN4XZG (the 5th image)
And this one where he wears horseshoes even though his paws aren’t shown (dated 1974): https://comicvine.gamespot.com/playhour-1033/4000-772707/
I apologize if this comes off as weird in any way, I just find it cute for some reason.