I wear a Bass Pro rebranded Scala outback hat all winter long. It came with a cheesy and tacky camo hat band so I wove one from some cheap leather lace from hobby lobby one night when asked to join my wife for a chick flick; I had to google the weave and found instructions on some paracord craft website. I put a leather antler burr on it as well. I get complimented on it by both men and women at least 3x a week.
In summer time I wear a Tilley TH5 hemp hat. I get compliments on it as well but not as frequently as my wool hat.
Both are water resistant, block the sun, help regulate the temperature on my head, look good enough to wear into work with my button up shirts, but are tough and durable enough to keep up with my outdoorsman lifestyle, can be washed at home, are foldable/crushable/packable, and move out of the way of my bowstring when hunting. My wool hat was probably $50 or so including the leather lace and my Tilley was a gift but they run around $75 I think.