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Thanks for the help. We associate ourselves with the “modern orthodox” community. However, many people in our community aren’t actually “modern orthodox”. Back to the hat, Rav Soloveitchik ZT”L from YU as well as the current Rosh Yeshiva, Rav Schachter, both wore hats as well. I don’t think it’s that far fetched. Unfortunately, there is a negative connotation with the hat due to how some people who wear it act. I agree totally with those who wrote about “Kibud Av”. It is, after-all a D’oraiysa, so it should be valued tremendously. The question I’m asking everyone though, is how to discuss it in a respectful way. What points/pointers should I bring up? How should I initiate the conversation, etc. THANKS!