"Effortlessness" may not be the best word to encapsulate what I was getting at, but I think you distilled it pretty well @Fuuma
I guess the theme of what bugs me most in style; in people; in bikers; really anywhere, is a lack of genuineness. Calling a person's style "nearly effortless" is just another way of saying that they've figured their shit out a while ago and - perhaps as you suggest - edited their wardrobe to a point where they can just throw on anything and nail it in their own way. Comfortable. Unthinking. Doing. Wu wei. A guy can still look great without being there, just like a guy can hop on a fancy bike and feel all kinds of passion for it.
But: Distilled essence expressed. That's the real deal. In my (apparently unpopular) opinion.