Luke is widely regardedm as being either a Gentile or a Hellenized Jew which means he or she would not have been subject to the laws of Deuteronomy.

That said, in ancient Rome, cross dressing was forbidden outside Saturnalia, where it was encouraged. But the respect show to cross dressing as part of religious practices that suggest there may have been some leeway here, especially in satellite states or conquered lands of the Empire. Also, neglect comes into play. Rome wasn't particularly interested in upholding the religious laws of those they conquered, even as they didn't squash them comoletely. Mostly they just didn't care.