Hey, assume you're in 'berta so something to consider is Thursday boots are $200 USD which at current rate is $255 CAD. I believe duty is an additional 20% (but if I'm incorrect, someone please chime in). That brings the boots to $306 CAD.
That puts you in the same price point as Canada West and just shy of Red Wing and Wolverine .
Nothing against Thursday and I don't know how they compare to Canada West / Red Wing / Wolverine (or if any of those brands have Jodhpur style boots) - just thought it might be helpful to give you other options!
Navy pants. Light blue/light red striped OCBD. Brown wingtips or 1000 mile style boots. With or without a knit or wool tie.