Same question is basically applicable to all those city flags. Are those modern ones? These days every city has a flag for some reason….
Fair, I honestly do not know when they are from, but we use the same flag for the US for coins from the 1800s but I understand your concern
This flag was created iun 1931
https://www.araldicacivica.it/pdf/decreti/ar/arezzo.pdf
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