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Strangeattractor comments on Tell me what hat to buy - Less Wrong Discussion
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You might want to look into Panama hats for the summer. They are sort of dressy, and could be worn with a linen suit to more fancy events, for example.
More casual is a Tilley hat, though I'm not sure it would be that much different than the "floppy boonie hat" that you have already.
Winter hats are a different thing. I tend to like ones made from Polartec polyester fabric, since it's warm and washable, but I'm not sure how fashionable they are. Puffin Gear is a brand name of winter hats that I like.