I wear hats regularly and have for some time. Exactly what kind has shifted a bit over time, but I have a few types including fedoras, gamblers (I think it's called), and caps. The caps are for more casual use or maybe rain -- I don't want my nice hats taking water damage -- the gamblers are for better sun protection since they have the widest brims, and the fedoras are for a nicer look, and I have some in straw and felt so there are options for all seasons with those.

FWIW, I feel like the trickiest thing to get right is middle levels of formality. Things are so relaxed at the casual end that there's a lot of freedom, and when you get to suit-level or above, things are relatively fixed. It's outfits in what I guess might be business casual area that seem harder to put together well, at least for me. So I think a guide along those lines would be helpful.

I don't have a monthly budget for fashion purchases. I get new items on an as-needed basis, so purchases tend to be infrequent and l spend what I need to to get what I want.

Generally, I'd say the overcoat looks best, but I think it can be a bit formal, so for something a bit less formal, I'd say the peacoat.

I can't always keep up with reading and posting, but I do try to at least skim posts every now and then and like something when I do in order to not be totally inactive.