Augustine of Hippo

But let not any suppose that the Lord's feet were by this woman bathed in ointment after the manner which the luxurious and debauched use. In all things of this nature, it is not the thing itself, but the mind of him who uses it, that is in fault. Whoso uses things after such sort as to pass the bounds observed by good men with whom he lives, either has some meaning in what he does, or is vicious. What then is vice in others, in a divine or prophetic person is a sign of some great thing. …

Catena Aurea by Aquinas ↗

Ambrose of Milan

It is possible therefore that they were different persons, and so all appearance of contradiction between the Evangelists is removed. Or it is possible that it was the same woman at two different times and two different stages of desert; first while yet a sinner, afterwards more advanced.

Catena Aurea by Aquinas ↗

Jerome

A woman came to him with an alabaster jar of expensive perfume, which she poured on his head as he was reclining at the table. No one should assume that she who poured the perfume on his head is the same as she who poured it on his feet. For she washes with her tears, wipes with her hair, and is clearly called a prostitute. However, nothing of this sort is written about her. For the prostitute could not immediately become worthy of the Lord's favor. …

Commentary on Matthew ↗