Masculine and Feminine noun genders (and Neuter as well, incidentally) as semantically meaningful properties of a noun disappeared before the emergence of English per se. Which is to say, semantic implications/limitations of grammatical gender are rare and inconsistent, among the Germanic languages, and English (even in the 7th century) was no exception. In Old English (5th to 11th century), any historic relationship between grammatical gender and semantic criteria is completely lost. "Wif" meaning "woman" is neuter. "Wifman" likewise meaning "woman", is masculine.

There is a tendency, to be certain, for earlier semantic implications to be reflected. Essentially all words for "warrior" (secg, cempa, wiga) remain masculine. But a compound like "wifman" emerging during the Old English era itself acquires its inflection not via a semantic imposition on grammatical gender, but by simple phonetic analogy (i.e., words ending in "-man" mostly follow a "masculine" declension, so this one likely should too).

As for when grammatical gender ceased to be represented phonetically, there is no easy answer (since some of the effects of these inflectional distinctions are still represented today). But the Late Middle English era struck the final blow, with a great many final vowels which were phonetically and inflectionally distinct in Old English being at last dropped, and with many inflectional affixes seeing their vowels conflated (though that had been going on for a long time), such that plural -es and -as and -e and -a are no longer distinguished, and many of these words are furnished with the -es plural which has become our convention, as a remedy (where -es/-as was indicative of masculine noun gender, in Old English).

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One theory argued by linguist John McWhorter in his book "Our Magnificent Bastard Tongue" suggest Viking contact beginning in in the late 700s is to blame for Old English losing its gendered nouns. To sum up what McWhorter believes, Vikings speaking Old Norse conquered England and were forced to mingle and speak with the native, Old English-speaking population, resulting in a "mangled" and more simplified version of English. This then spread as children grew up hearing the streamlined grammar and continued to spread.

The main supporting argument for this is how Northumbrian Old English, where Vikings had contact, began to shed endings and noun gender much quicker than Old English dialects in the southern part of England where there was no Viking contact.