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Yay for you getting all 5 right! I intentionally chose those as they have fairly unique silhouettes (although I wanted to make it a bit more challenging with the orcs) and you don’t necessarily have to go to any raids to see them (even Kel’Thuzad has his little outdoor playground hovering in the Borean Tundra). But I still imagine there are going to be people having difficulties recognizing them. Hence the little ‘Dating Game’ hover text.

I’m really excited to see our new armour sets as well, especially once the designers get their crazy “this has to look Asian” over-the-top designs out of their systems. The longer they work on this Asian influence, the more subtle it can be, yet stay clear enough. At least I hope that’s where the development is going to end up.

The one big problem I see with the new things they come up with — and this is where the problem with my silhouette improvement suggestion lies as well — is that we might not be able to mix some of the new armour stuff with old armour sets.
You can already see this when you look at the improvements in texture across the expansions. When you look at, say, the Judgement set — very well-liked throughout the community — in isolation, it is awesome. The colours are ranging from black to orange and yellow, it looks very heroic and mysterious (hood!), and who didn’t envy paladins for their awesome tome-and-sword shoulders back in the day? (I know I did.)
Now, if you put the set next to the most recent paladin tier set, tier 13, the Judgement set suddenly looks less good. It looks flat, void of detail and the materials are off (the metal looks so much shinier on new armour). This effect is even more visible with some leather or cloth sets. Where in early sets you couldn’t tell if there were metal or wood pieces in the costume or if it was maybe embroidered into the cloth, more recent armour sets show that difference very clearly. Remember the druid tier 12 armour? Whether you liked it or not, you could tell that some parts of it were carved wood and scorched bark.

Now, if you try combining old and new armour pieces into one transmogrification set, you may run into problems for these exact reasons. It just looks weird.
If they continue down the road of making more armour pieces stand on their own (like they announced with belts), we might end up with a sort of divide in the sets you can combine safely. A pre-surface and a post-surface phase, if you will.

I’m sure Blizzard is contemplating this issue already, and I’m assuming they haven’t really come to a decision yet. Belts are, after all, more accessories than anything else, and a belt that stands out from the rest of your armour is less destructive to transmog sets than a pair of trousers not matching your shoulder pieces (for whatever reason).
If you’re looking for difference in your sets: great. If you, however, are looking for some unity throughout your set (and maybe have one or two pieces stand out by being different — like a belt for example), then mixing and matching pieces from past expansions with new stuff will get harder and harder as technology gets better.
Blizzard could fix the issue by retroactively fixing the old gear to fit the new (in the future) models, but this would mean a ton of work for them (which they would have to do all over once they make another jump in what’s possible). I would rather see them put these countless hours into new content. (This is also why re-hashing old content and using it as new stuff is problematic and gets old quite quickly, but that’s a topic for another day.)

TL;DR: I have no idea. There’s problems to any approach Blizzard might take in the future, as the new stuff doesn’t overwrite the old, but adds to it.

z

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