Growing up most of the women I saw in synagogue did not wear kippot (head coverings traditionally worn by men in Judaism), tallit (prayer shawls) or tefflin (phylacteries, described more below). And when I saw the odd woman who did, I thought she was just that, odd.
So, you can imagine the discomfort I felt experimenting with wearing this ritual garb when I started thinking about becoming a rabbi. Wearing a tallit was fairly easy. I bought a beautiful multicolored tallit and loved the feel of enveloping myself in it. It felt a bit like God was reaching out and giving me a hug. Wearing a kippah was a bit harder. It was not physically uncomfortable, but I hated how it messed up my hair. Vain, I know, but true. I just did not like the way it looked. Wearing teffilin was harder still. I was given a gift of teffilin which were way too big for me. They had large black leather boxes and thick black lengths of leather that I needed to wrap around my arms. They were uncomfortable to wear.
Having written my undergraduate thesis on Jewish Feminism, I knew that women had fought for the right to wear these ritual objects. I wanted to embrace the practice of wearing them. But even after years of trying, I still feel ambivalent about wearing a kippah, and have stopped wearing teffilin entirely.
These ritual garments are important symbols with in Judaism. A religious Jew defines him or herself by how he or she dresses. In more liberal circles, a rabbi often stands out in the crowd by wearing a kippah or a tallit. The donning of these garments for prayer is a meaningful way to state ones intention to pray and forge a deeper connection to God. Some Jews believe that wearing these garments is a command form God that they must follow. There is great historical and emotional weight attached to the wearing of these garments.
I struggled for years to become comfortable with my own practice of wearing a kippah and tallit when I pray, but not wearing a kippah at other times as many of my colleagues do. In addition, since I found teffilin to interfere with my ability to pray rather than to enhance it, I no longer wear them.