KC:
You have several options, depending on your emphasis. You could consider fedoras, tweed driving caps, "ambassador" caps, or other fur hats, depending on your preference. Because you often wear a sportcoat, almost any of these could work for you. The fedora might be the most flexible, if not the most warm, as it would also protect during sunnier months. (I also happen to find fedoras the most stylish option.)
Prices for fedoras range far and wide, depending on the style and quality you want. Some decent vintage felt could be had on Ebay for as little as $50 if you find the right auction, or you could go custom and spend anywhere from $275 to over $500, with either vintage or new felt.
On the other hand, there's nothing wrong with Akubra hats--my Akubra Leisure Time is my favorite everyday hat. It's not top end, but it's good, solid rabbit fur felt that has been taking an 11-year beating and still looks good.