Why a 99 Flake isn't called a "99" because of the price

The “99 Flake” name does not indicate a 99p price. The Flake chocolate bar was created before UK decimal currency existed, so “99 pence” was never part of the original context. The origin of “99” is uncertain, with two main theories. One theory links “99” to an Italian monarchy bodyguard said to have exactly 99 soldiers, which Italian gelato makers allegedly used as slang for top-quality items. A second theory connects the name to an ice cream shop opened in 1922 at 99 Portobello High Street, Edinburgh, where Flakes were reportedly broken and placed in cones. Another related account ties “99” to Cadbury advertising for a Flake ice-cream sandwich, where customers were told to ask for “99.”

"But, here's the twist - barring maybe a year or two when prices converged, it's never been meant as a 99p ice-cream and the 99 in the name is nothing to do with the price. After all, the Flake chocolate bar was invented when the UK was still using the pre-decimal currency, and there was no such thing as 99 pence."

"The guards theory In the days of the Italian monarchy, the King had an elite bodyguard of exactly 99 soldiers. Because these guards were considered "first-class," Italian gelato makers in the UK adopted "99" as slang for anything sold by Italians that they considered top quality. However, the fact that the Cuirassiers Regiment generally consisted of 80 soldiers, not 99, is a tad awkward for this theory."

"The Scottish theory An Italian immigrant named Stefano Arcari opened an ice cream shop in 1922 at 99 Portobello High Street, Edinburgh. He reportedly started breaking large Flakes in half and sticking them in cones, naming the dessert after his shop's address. The family has supported the claim, and I can find records of a Stephen Arcari as a confectioner trading from that address."

"Interestingly, for this story, their advertising called the flake ice cream sandwich a "99", and shoppers were advised to go into a confectioner and ask for "99". Why they chose that name is sadly unclear. That might be cause "Flake" was a classification of cocoa sold by Cadb"

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