Shalom,
In principle, there should be no problem with wearing a kippah during Mass. In fact, one of our members used to wear both the kippah and the tallit at Mass.
When we came to St. Louis, this member attended a Mass with us which was celebrated by Archbishop, now Cardinal, Burke. Archbishop Burke was the one who welcomed us to St. Louis. After Mass, one of the Catholic men attending ran up to the Archbishop to tell him that a Jew had just received the Eucharist. Archbishop Burke knew who our friend was and he responded: “A Jew just received a Jew.”
Since Vatican II, theologians and clerics have been working to understand the Church’s relationship with the Jewish people, both those inside the Church as well as those outside. It is going to take time to revise the narrative that has been present for 1700+ years.
The prelates use of a kippah-like hat, called a zucchetto, is a tradition dating back, I believe, to the 1300s.
Regarding your desire to wear the kippah, I would advise you to respond with prudence and love. I know of no rules directing what the laity may wear. Today, it is scandalous the way some people come dressed to Mass. If your pastor doesn’t forbid you to wear it, then wear it. However, if wearing it causes distress amongst the laity, then out of love for them, I would not wear it. It is going to take time before normal Catholics get used to Jewish traditions.
