That's what I wear most days in cold weather, and am frequently complimented. I'd wear it year-round, 'cept it's too hot. By carebear's definition, it's a fedora, apparently. It certainly does not need a suit to complement it. Most folks seem to think it's a "cowboy hat." That being said, I also dress like a big boy, meaning no sneakers, shorts, sandals, sweatpants or other silliness. Tend not to wear sweatshirts or sweaters, either, but that's just me.
Downsides:
1. When shopping, etc, it always occupies one hand, so I sometimes leave it in the vehicle. I could wear it inside, but that just seems poser-ish. On the upside, it is not so bad as an improvised shopping basket.
2. Due to 1, once or twice per season I have to go back to the Steak n Shake or wherever, to see if they have my hat in the lost and found. So far, they always have.
3. Sometimes blows off in the wind.
4. In the car, it sometimes bumps into the head-rest or sun visor. But then, I am too tall for the little vehicles I am driving now-a-days. I will go back to the full-sized pick-up as soon as feasible.