I'm responding to this because it looks like we're in the same area. I'm in "willinois" . Totally new, so I can't speak to your question other than to say my trainer told me today to just wear the boots I already have into the ground, and that probably the next thing I'd want to buy would be half-chaps (I had asked if I needed to replace my DSW "paddock" boots with real paddock boots"
Anyway, she told me I would want to get fitted for my first pair, and that there is. Dover store in Libertyville. Thought I would pass that info along.