Howdy and welcome to the western world
Is it very windy where you are? If not, then I'd really suggest a palm leaf hat. They stand up to rainy conditions a ton better than a regular straw hat and they are not as hot a felt hat. You don't need to steam them to shape them and they can look very snazzy, depending on the style that you get.
If it is windy, I'd go with a felt as they stay on better (coming from someone who rides in the windy plains in Texas
). Color and particular style only really matter if you are showing. Whenever I'm shopping for a new hat, I go to a western wear store and just try hats on until I find one that fits well and I like the look of. If you aren't sure how you should shape it, you can normally just go to the hat counter where they have a steam machine and let the guy/gal shape it for you.
No matter what you get or how you have it shaped, you will likely feel like you look goofy until you get used to it LOL. I've been wearing cowboy hats most of my life and I still feel a little goofy-looking when I get a new one.
As for boots, I have basically the same problem as you. My feet aren't terribly small (I wear a 8.5 or a 9, US sizes) but they are really super wide. The only pair of boots I've ever bought that were wide enough right off the shelf are my steel toe Justin Gypsy work boots...but they have a thick enough sole that they aren't safe to ride in.
For riding, I like my Ariat Quickdraws. They only come in B width, but the square toes make them fit a little wider than the regular round toes. Basically, what I do when I get a new pair is soak them in hot, almost boiling, water for 15-20 minutes until they are really soft and saturated and then I wear them until they dry. After they are dry, I oil the heck out of them and that gets them broke in and comfortable. My newest pair was about $150. Not sure where that fits in your budget or even if it does.
Justins tend to go a bit cheaper but they never seem to last me as long. Also, my feet are really particular about the insoles in my shoes. Most shoes make my feet hurt within just a few minutes but both my Ariats and my Gypsys have a good enough insole that they are comfortable to walk around in all day. However, when I was younger and my parents bought my boots, I used to wear Justin Ropers because they were cheap to replace when I outgrew them or wore them out. They had insoles in them like concrete. It was more comfortable to walk around barefoot on the rocks than to walk in them LOL.