As a rule, there shouldn't be anything that is a separation between a man's head and the tefillin, so seemingly a wig would be a problem. In Igros Moshe Orach Chaim Chelek 4 Siman 40 Ois 18, Rabbi Moshe Feinstein addresses the question of someone who wears an easily-removed wig at all times and would be embarrassed to remove it in the synagogue. He says that such a person should put on the head-tefillin in the synagogue, while wearing the wig, without saying the bracha, and that later, at home, he should put on tefillin without the wig and with the bracha. Are there any makilim (lenient halachic decisors) in this matter that permit someone to put on the tefillin lichatchila, with a bracha, over a wig, in a case in which asking the person in question to do this double wearing may be asking too much?
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