Where did Maimonides find his liberal stance regarding women and talitot (and, necessarily, tefillin as well)? In tractate Eruvin, 96 a:
Michal the daughter of King Saul wore tefillin and the Sages did not attempt to prevent her, and the wife of Jonah attended the festival pilgrimage and the Sages did not prevent her. Now, since the Sages did not prevent her, it is clearly evident that they hold the view that it is a positive precept, the performance of which is not limited to a particular time. But is it not possible that they hold the same view as R. Jose who ruled: It is optional for women to lay their hands upon an offering? For were you not to say so, how is it that Jonah’s wife attended the festival pilgrimage and the Sages did not prevent her, seeing that there is no one who contends that the observance of a festival is not a positive precept the performance of which is limited to a particular time? You must consequently admit that he holds it to be optional; could it not then the case here also be said to be optional?
So we already have the nice custom of women’s “ownership” of the days of Rosh Chodesh, and the views of the Talmud and Maimonides that they have permission to wrap themselves in talitot and put on tefillin – what’s the problem, then? Why is it that each time the Women of the Wall try to keep the explicit halacha according to the Jewish sages, the police come and arrest them and stick them in the Russian Compound in Jerusalem for the duration of the day?
Those who object to the prayers of the Women of the Wall rely on a ruling by Rabbi Yaakov Halevi ben Moshe Molin, the Maharil (1360-1427), who is considered the earliest authority on the customs of Ashkenazi Jews. He ruled that women who wear a Talit Katan which must have corner fringes do so out of haughtiness, which is a negative quality. Based on that, the Rama, who is the primary Ashkenazi commentator of the Sephardi Rabbi Yosef Karo’s fundamental halachic text, the Shulchan Aruch, rules that it’s better for women not to wear a talit – and of course not tefillin, which must be kept clean and 15th century women where not the most hygienic persons.
So, for the concern regarding haughtiness, Ashkenazi women were forbidden to wear talit. The problem is that there are several opinions regarding cases in which men are permitted to keep commandments that may be rooted in haughtiness just the same:
A bridegroom is exempt from the recital of the Shema from the [wedding] night until the end of the Shabbat, if he has not consummated the marriage. It happened with Rabban Gamaliel that when he married he recited the Shema on the first night. So his disciples said to him: Our Master, you have taught us that a bridegroom is exempt from the recital of the Shema. He replied: I will not listen to you to remove from myself the Kingship of Heaven even for one hour.
Sounds to me like a classic case of haughtiness: Rabban Gamliel decides he’s above the law, and even though he is about to undergo his first sexual experience with his new wife, he insists on saying the Shema, because his head is clear of improper thoughts even on such a tense night. And yet, our rabbi receives the approval of the sages of the Mishna, possibly because they realize that he knows himself well enough, and if Rabban Gamliel says his mind is clean, it must be clean.
Likewise in the area of wearing the talit katan with the fringes hanging outside the pants. According to all the greatest cabalists, this is a sign of haughtiness, and they much prefer that people keep their tziztis from flying all about (even the late Lubaitcher Rebbe objected to wearing the tzitzis on the outside.) But try and explain it to the hundreds of thousands of religious men who let their tzitzis fly as if they were the gold fringes on either side of Napoleon’s shoulders. And they’re forgiven. So why can’t we forgive the Women of the Wall?
Because they threaten the very spiritual identity of the State of Israel.