I did not grow up wearing a tallit or a kippah. In fact at my home synagogue we had black kippot for the men and little doilies for the women to put on their heads. Neither ritual item was really explained to us and why or why not we should wear one. As I got older and then married Arthur, who always wore both kippah and tallit but I didn't think much of it.
When my kids were at Solomon Schechter Day school it was required that boys wear kippot all the time and girls were allowed to wear them. Lital, my oldest and my daughter never wore a kippah at school but she decided to wear tallit and kippah when becoming a Bat Mitzvah. I hope I had something to do with her wearing a tallit as I had begun to wear one when she was much younger than 13. It was a Lakeside student who made me decide to wear a tallit.
I also started thinking that if I did not start to wear a tallit how could I expect Lital to wear one when she became a Bat Mitzvah in September 2001? That summer when I was on faculty at OSRUI where we lead t'filot every morning and help our campers lead in the evening, I started wearing a tallit. No one said anything. At camp it was acceptable to wear a tallit or not. No one said anything to me. When I got back to Lakeside I started to wear a tallit for the High Holy days and slowly I added this new custom to whenever I pray. I especially wear a tallit when I know there will be a Torah service. I don't always wear a tallit but I do have a small collection in my office. At confirmation I always offer some of my tallitot to our girls and if you look at the pictures on the wall outside of my office you will see some of my tallitot. Enjoy and have a Shabbat Shalom.