I've ordered a really nice wool hat from DebThorpe on Etsy: https://www.etsy.com/shop/debthorpe

She knits thick wool hats in a lot of bright, colorful patterns. It's definitely warm enough for walking around town when temperatures drop into the 30s-40s. The wool is really thick, so it might be too toasty for snowshoeing or cross-country skiing when you're getting more of a workout.

I've also gotten nice knit wool hats at Pike Place Market. There's usually quite a variety, so you may want to check out the knit hats there when you're in Seattle.