For boots I really like the look of the Frye harness boot

But they're proving a little hard to find out here among the conifers so temporarily I was thinking of using my hiking boots to ride with? They are these exact ones:

And as for a helmet, I'm looking at a Troxel, I really like the Cheyenne style it's kinda different.

ANYWAYS thoughts on these brands and my boots? Or completely different suggestions that you think would be radical? I like the idea of stuff that is Western but versatile and pretty/casual. Of course and GOOD QUALITY. I guess I should mention for either of these things I have a price range of around $200 but will budge. :P
EDIT: Oh also, are jeans OK?