As it happens, I wore my black hat today. I rarely ever wear it, but somehow I had the urge this morning. It produced a few stares from the chassidim at Mincha who are used to seeing me in a gray or taupe hat. But thanks Helpful for letting me know that a Stetson is also oisgehalten. Is the tear drop crown an acceptable variation as well? As to the Homburg, when I was in college I made a pact with my chavruseh and best friend at the time, that we would both buy homburg hats on our 40th birthdays. When I turned 40 last year I called him and asked him to be mochel the chov as I don’t feel “old” enough to wear one, and we agreed to push off the purchase for another five years and reassess the situation then. And indeed I do most definitely wear a straw colored straw hat from Memorial Day until Labor day. I actually have two of them. One was a gift from my boss.
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