I've always held onto particular pieces of gear for all of my characters, either because I've liked them or because getting them was significant for me/my character in some way. Unfortunately, I've ditched a lot of pieces too, since I ran out of bag space long ago.
At any rate, transmogrification for each of my alliance characters has been a unique journey. Some are easier to figure out than others. Others have required some trial and error. One theme has remained true throughout: my characters and I all seem to be more drawn to simpler sets rather than flashy ones. With all the gorgeous options out there, we opt for simplicity. Go figure! Flashy or not, I think they look good.