I have watched a ton of what not to wear, but like you said, they focus more on the right fit or chosing the right clothing for one's lifestyle/occasion. I can do that with my eyes closed!

My problem is putting together the things I already own in ways that are updated (maybe with accessories and things).

I didn't think of looking at online sites though, that makes sense. I do flip through catalogs, but I only get catalogs from places I order (like Athleta, jcrew and Sundance) so they just show me more of what I already know. I'll try doing more browsing online...good idea!