Well...I have one of each, plus a straw hat, and I identify as an English rider... LOL
I most recently bought a cream hat because my show shirt/pants/chaps are all cream so the black looked silly. For just hacking out/small ranch shows I wear a black one because it looks nicer on me, and I won't get it dirty as easily. My tack is a dark oil, not reddish at all, so I find that any of the colors work. Posted via Mobile Device
What color is your saddle blanket/pad (or are you just uskng the black pad you have pictured) and what color is your outfit?
I have a cream straw hat for my (future) show outfit. My saddle blanket is tan, cream, brown, and turquoise. My show outfit will be a turquoise shirt, blue jeans, brown chaps, and brown boots with turquoise stitching. I don't have my tack yet, but I'm going to try to go with a medium oil (like yours), hopefully with rawhide accents on the headstall and reins. So, the cream straw will work perfectly with that.
I think your hat needs to match your outfit and saddle blanket/pad, not your tack. Posted via Mobile Device