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I can't necessarily offer an answer here, but I can give you a bound at least. I was able to find this 1703 geography of the Kingdom of Naples that explicitly calls Italy a boot, so "some time before 1703" can be said for sure
Machine translated:
I'm fairly sure the Strabo bit means "we've known it was this shape since Strabo" rather than "Strabo said it was boot-shaped"
To speculate a little more, I think the style of boot that Italy looks like started off as riding shoes developed in 10th century Iran (heels are good for staying in stirrups, apparently). If that is correct then it can't be earlier than the 10th century since there weren't boots that Italy looked like
I wonder when the high enough heel was invented to see the resemblance.