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Further explanation on Rabbi Eliezer ben Yaakov's comments

In this text Rabbi Eliezer understands the term "Kli Gever" (the apparel of a man) in a very narrow sense to mean weapons of war. The Hebrew word "kli" has broad implications in the Bible: it refers to vessels and utensils, as well as garments. Rabbi Eliezer understands war as a strictly male pursuit; hence the "kli" (utensils) of men refer to pieces of battle gear. This view is supported by later rabbis elsewhere in the Babylonian Talmud (Kiddushin 2b) who argue that is appropriate for men to engage in war, but not for women to do so. Rabbi Eliezer's primary concern seems to be that women should not transgress male social roles by going to battle. He understands this verse as a prohibition on women using the tools that would lead them into men's social arena. On the other hand, he interprets the prohibition on men wearing women's accessories to be a much broader ban, prohibiting men from adorning themselves to look like women.

A similar view is reflected by the Targum Pseudo-Yonatan, an early Aramaic translation of the Hebrew Bible, which understands "kli gever" (men's apparel) as strictly applying to ritual garments: tallit (prayer shawls) and tefillin (phylacteries). Pseudo-Yonatan shifts the focus of the verse away from cross-dressing per se. Instead he focuses on restricting women's access to ritual participation. Both Psuedo-Yonatan and Rabbi Eliezer are concerned with circumscribing women's roles in public society, and are less concerned with the actual clothing that women wear.

The opinion of Rabbi Eliezer seems to indicate his understanding that women are prohibited from wearing men's clothing when it encourages them to "act like men." Men, on the other hand, should not "look like women" at all. This interpretation is echoed by the Tur, a Medieval Jewish law code. It is interesting to note that, while this position is troubling in that it reinforces misogyny and limits men's freedom to dress in a way that feels authentic for them, it is still a very non-literal reading of our central verse. The Bible appears to be putting a total ban on cross-dressing, but these interpretations make the prohibition a great deal narrower.