I used to have a Watership vineyard haven hat in breathable nylon but now I use the Tilley LT5, which is very similar in materials and quality. I’m kind of particular about the style of my hat and I found the Vineyard Haven hung a little low on my head for my tastes and the LT5 was more my style. But maybe that doesn’t matter for you…
Neither the Watership nor Tilley hats have garish logos and I consider that a big issue. Whether in the city or the mountains, I’ll be damned if I’m going to go walking around with somebody’s logo stamped on my forehead. So I wouldn’t even consider OR’s hats because of that. But again, that’s a personal issue…
I have no experience with waterproof hats. Both the LT5 and the Vineyard Haven hat in breathable nylon are water repellent, which means they protect from snow and drizzle (the rate of evaporation due to heat from my head is greater than the rate of moisture from snow or drizzle), but they leak under torrential downpours. When that happens, I tuck my poncho or rain jacket hood under the hat to fully protect me. Once the downpour stops, I tuck the hood back down my back and my head heat soon dries the hat back out. Again, this refers to breathable nylon (supplex with DWR), not eVENT.
One thing to consider is buying the hat larger than normal so you can wear a wool knit hat and/or poncho/rain jacket hood underneath. A too-large hat is also more comfortable in summer, but then if you’re thinking of Event, that’s probably not an issue for you.
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