Well, I can see why the expression "It fits to a T" would derive from the T-Square, used by carpenters before more sophisticated measuring devices came along. As to why the T-Square is called a T-square, I would think that's simply because the instrument is shaped like a T. So when something fits you to a T, it means that it fits as well as a carpenter's fitting together of two pieces of material--and if he's a good carpenter, that would be a very good fit. (Years ago, I can remember old time carpenters performing almost magically with that T-square, as they turned it one way and another to get the right angle and fit for another piece they were putting together.)
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