Works fine with (and definitely improves the looks of) a road crank with the chainring on the inside, but how many track/ss/fixie cranks have a place for a chainguard? I have thought about this myself, but right about that time Miche Primato cranks started popping up all over ebay at prices I couldn't resist.
Besides, if you wear shorts, there's no rolling up to do- the only thing you have to worry about is your laces... easy enough for someone living where the temperature rarely drops below 40 degrees or so...