A K&N will filter better if its a little dirty.
A visual inspection is usually enough to tell if it needs cleaning, and by that I mean lightly caked-on dirt, or you can see more brown that red.
K&N's do flow better, but it is at a minor filtration penalty. If you clean your K&N too often, all youre doing is letting more small particulate in, more often. Then the second line of defense has to pick it up (i.e. your oil and oil filter - and thats not a good thing).
An Outerwears will not stop smaller particulate, theyre made for larger particulate and repelling water.
If your seeing dust in the boot, then either its WAY too dirty, OR it wasnt oiled properly before. If you get a **** load of mud on it, clean it immediately! If the mud dries on the K&N, it can damage the filter media and let all kinds of **** in.
I always recommend running an Outerwears when using K&N's, but you still have to maintain the filter properly.
Hope that helps.