I've been a Closed Toe opponent since the first silly looking pair hit the market years ago. I tried on the Josh Twelker boot at the boat show last weekend and they convinced me to convert. They're down right luxurious feeling. I'd say they're medium stiffness. I found that they had great hold hold even without running the upper lace system tight. I'm looking forward to riding them this year. If you want something slightly stiffer, the Faction boot is pretty much the same thing, but a tad more rigid. Both boots look pretty awesome I think.