Personally, I love wearing hats, especially during different seasons. My favorites are baseball caps and beanies, but I’ve recently gotten into personalized bucket hats personalized bucket hats . They’re a great way to show some personality and you can always find some cool designs.
As for what's considered "douchey" headwear, I think it depends on how and where you wear it. Beanies can be fine in warm weather if they're lightweight. Baseball caps in a restaurant might be a bit much, but it also depends on the place.