not sure this is the right place for this question. try these?

https://www.google.com/search?q=waterproof+hat&client=safari&hl=en-us&prmd=sivn&sxsrf=ALiCzsaSVkFcucNJSvz-C7ZYp7oIgiTbng:1666029375798&source=lnms&tbm=shop&sa=X&ved=2ahUKEwioxISJ6-f6AhUiFlkFHQ-1DKAQ_AUoAXoECAEQAQ&biw=393&bih=660&dpr=3

https://www.reddit.com/r/AppalachianTrail/comments/63kji2/what_is_your_favorite_waterproof_hat/?utm_source=share&utm_medium=ios_app&utm_name=iossmf

r/malefashionadvice r/hikinggear www.rei.com

These are high end rain hats

Gortex Rain Hat Pro

Stylish bucket hat with wide brim, neck flap and wind cord on Amazon.

I’m 38. My mother gifted me a Barbour hat a few years ago. I get a good amount of use out of it. Hat

Get yourself a sturdy umbrella. Wear whatever hat you want. In colder wet situations I recommend a fleece or wool beanie of some sort. But as you likely know there are wind tunnels between the skyscrapers which will make the rain and snow go sideways. You can use the umbrella as a bit of a shield so it doesn’t hit your face from that sideways action. I used to commute daily to Manhattan and this was my system. Always have an umbrella with you in the city. Pair it with a long coat, at least 3/4 length for more body coverage.

Can we ask why not just go with a rain jacket?

yes. feel free to ask.

well. I have a rain coat. it has no hood. it's one of those kinds that is hoodless, and i prefer it without a hood.

any umbrella suggestions? this doesn't put me off my hat hunt, but this may be the next thing, if necessary.

Well in the event you decide to dabble in rain coats I’ve had a lot of success with the ones from Uniqlo. Very water proof, insulating layers, not too large, pretty stylish, and most come with hoods that have a degree of structure and a small brim built in so you aren’t getting rain in your face. Also as someone else said r/malefashionadvice will probably give you a lot more insightful answers

If you do decide on/find a good hat though report back.

I made a decision. The Seattle Rain Cap from Outdoor Research.

Ikea bucket hat. When my son insisted on owning this..I thought he was crazy, and he is, but this hat is wicked! https://www.ikea.com/us/en/p/knorva-hat-blue-50447338/