As far as pocket square goes I think you're safe to try something with a bit of colour and pattern, maybe gold/ burnt orange?
One thing that is important, do you have matching belts for your shoes? Also I think gold buckle...
Every 4 weeks, I go to an expensive place.
I'm going to start doing the expensive place every other time and maybe fit in more cheaper places inbetween and then have the expensive place set the style again.