TEFILA: From turbans to kippas

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כי פריס סודרא על רישיה לימא עוטר ישראל בתפארה     
Blessed are You haShem Who crowns Israel with glory”.
This blessing was established by the rabbis in Talmudic times to be said when a man was covering his head.  What kind of head covering they used in those times? The word the Gemara uses issudar. sudar (which Maimonides renders sadin) indicates a piece of fabric of different sizes for different purposes.  It could refer to a handkerchief, a bed-sheet or a long scarf that was wound on one’s head as a turban. Covering the head was a common practice among Jews, and mandatory at all times for Tora Scholars (see Maimonides MT de’ot 5:6).  Many rabbis from the post Talmudic times (geonim) asserted that the sudar the Gemara refers to was a turban. Therefore, only in places or cities where a turban is worn this berakha should be recited.  Other Rabbis (Tosafot) thought that when the Gemara refers to the turban is indicating the standard way male Jews would cover their head in those times, but the recitation of this bearakha should not be limited to a turban, but it should be said for any kind of head covering. And that is the opinion of Rabbi Yosef Qaro in his shulhan ‘arukh (46:1) that this bearkha is said for any kind of head covering “When one places a hat or a turban on his head he should say ‘oter Israel betif-ara“.  
The rabbis also debated about the connection between covering our heads and God crowning us with glory.  The author of the Tur, Rabbi Ya’qob ben Asher said that his father, the famous Rosh, when saying birkot hashahar, would stop before saying‘oter israel betif-ara and at that moment he would wear his Tefilin. After wearing the head Tefilin he would say the berakha “Blessed are You HaShem… Who crowns Israel with glory” indicating that in his opinion this berakha refers (or includes a reference to) the Tefilin, which Jews consider a “glorious crown” (pe-er).  
Rabbi Yosef Qaro (siman 46), perhaps viewing the Rosh tradition as a private practice, said that this berakha refers to the traditional head covering (a hat or a Kippa), which by reminding us to be God’s fearing Jews (morat shamayim) inspire us to behave in a way that represents and reflects haShem’s glory.