Ive been wanting to wear a hat more often now that its gotten cooler. Its something I definitely have to build up to tho. The fairly easy to pair colors but I still have to figure out what style of hat suits me & my face/build best. So far Ive been liking Homburgs & medium brimmed fedoras w. dented crowns. Wide brims (except for panama hats) dont seem to work well with my face, same with very narrow brims (like many trilbies). Ive found to prefer stiffer hats rather then floppy/soft ones (like the typical "indiana jones hat").
Homburgs are certainly a bit more formal, which is why I wear medium grey one ATM rather then black. That one also has a pinch, which is somewhat atypical for homburgs, but it certainly makes it a more versatile every-day hat. Im still looking for a brown one in a similar style. Of cause none of these hats should be worn without a suit & tie as well as appropriate shoes.
One nice "gadget" Ive found on amazon yesterday was a transparent plastic rain cover for hats. All hats, wool or fur, dont really like to get wet & can loose their shape. Ive ordered some and if these work & fit well it would certainly be incredibly useful. Since these covers can be folded very small its easy to always keep one in your coat or jacket when wearing a hat as to not be surprised by the rain. Also has the advantage of turning any hat into a rain hat.