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					Originally Posted by bling trade  Obviously, hats aren't trendy, but I've seen guys pull off these hats:
 cotton, wool, or cashmere borsalino/capas/newsboy (biz casual),
 wool houndstooth or herringbone walking hat (biz casual, but more style-y)
 wool/fur trooper (cold weather)
 cotton fisherman or train conductor (casual)
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 Zero need for cold weather hats. I'm not a farmer, as Flinty is wont to say.
Absolutamente no! to a cotton fisherman, train conductor, or newsboy, as these are the very definition of costume hats.
The problem with the wool houndstooth walkers are (a.) I'm not Bing Crosby, though I think we should all aspire to be; and (b.) hats here are only necessary on pretty hot days or when it's raining. Let's put the rain scenario to one side because if you're wearing a trenchcoat you can get away with a cotton bucket hat and not look any more like a tool than many others on the street -- this ain't Carrie Bradshaw's Manhattan, at least not when it rains.
So it basically comes down to a linen or twill ivy (flat) cap -- single panel, as I said none of that newsboy look for me -- or a straw Panama.  So which would look less dorky with a navy or dark gray suit?  (I assume that either style would be marginally easier to pair with a summer weight suit.)
ETA that villagehatshop.com site has a stunning Panama porkpie called the Capetti that I would seriously consider wearing but it's $714.  WTF?