I'm wondering the same. Picasso's scramblings are only artsy because he was originally classically trained; you have to know about the rules to break them, as you say!
My two cents on the matter is that I've learned more from You Look Fab and this forum, than all the books I've accumulated about fashion and style combined. There's something about getting very specific and contemporary. If not it tends to get very abstract and widespread, and not really very helpful. (Have a white shirt as a staple in your wardrobe, for example. Any kind of white shirt? What will I wear it with? I look awful in men's shirts! It's not even my style. What then?)
I've had MANY light bulb moments thanks to Angie and the members on this Forum. The importance of garments being current for example. There's no such thing as truly timeless clothes. No wonder I've felt frumpy and dated in my thrift store finds, even though they where textbook chic and classic. Ha ha! I will still continue to browse thrift stores, but I will be sure to pair my vintage finds with modern and trendy clothes from now on.
Other great advice picked up from here, is bookending, paying attention to silhouette and texture of the outfit, subtle matching, throwing away old prejudice about seasonal colors, and rocking flat and comfortable shoes! Looking forward to learning more and become a better dresser!