I'd ask also for advice at the shop you get your boots at.
That said, if you are going to buy boots, you might look into the Burton ones that reduce your footprint on the board. Also keep in mind that with the binding in place, your foot is going to be elevated several cm relative to the base of the board, and you're also likely to be riding at an angle (20 degrees-ish, maybe less, maybe more) which is also going to reduce the probability of toe drag.
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