Boba Fett probably has my favorite helmet. Unfortunately a lot of the appeal behind the character got ruined by Lucas. Essentially what I found appealing and what I suspect the less enthusiastic Star Wars fanbase (those who didn't read the comics or get deeply entrenched in the EU) found attractive was his mysterious quality. He was just a force of a nature. Not only that he elicited a bit of a SWAT/Uber-Soldier Faceless Soldier that we all fear might come for us in some 1984-ish future, but not quite. That may be just me on that last part.
Part of what I like about this is that its clunky yet it still manages to pull off bad assery. Probably the visor.
I always assumed there was some substance given in that it sort of resembled the T Faced Helmets
Its known Vader had that going on with the Samurai Helms
And there is something about these designs... I'm slightly curious if its because Lucas was still in a slightly arthouse state after THX or what... but the problem I see later on with masks is that they try too hard to look cool... and admittedly they are cool. But they just don't have that *umph * to them. So to speak.
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Snake Eyes from GI Joe had a mask I quite enjoyed as a kid . Simplistic compared to the others, but it fits in and it draws upon the knight visor. The problem here is that the purpose isn't quite as clear. Or well I'll put it this way. The willingness for us to suspend disbelief isn't there. Whereas Vader and Fett have a huge bulky mass that could support a bunch of tech that our tiny non-engineer brains can't comprehend. Maybe tech heads find them all equally stupid *shrugs*
Another character that enters my mind in the ninja esque realm is Kroenen of Hellboy fame. Oddly I don't find him that memorable. Don't get me wrong I think his mask is cool. It may be the fact that he is a nazi ; my mind won't allow me to place him really high. Or it may be that there is something that just seems a bit too over-stylized (in that Underworld sort of Grit meets sleek) for my tastes at least.
The original Cyborg Ninja from MGS franchise seems as though he had potential in terms of presence were it not for the posturing ...
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Something to take into consideration is the fact that we are aware that we are being presented with something with an intended effect but at the same time isn't necessarily suppose to be something done consciously on the behalf of a character. By that I mean a character doesn't go out of their way to look peculiar or at least the filmmaker doesn't focus on this and considering how meticulous the design is we can assume that it is just part of the world.
When you have a character who is going for a certain look. If its done well it can work. Granted there is only one example I can think of recently and that is the Scarecrow from Batman Begins
Its not the most iconic, but thats partially why it works. It isn't perfected, but it has that slight artistic touch that one would expect from someone who makes their own mask . It helps that the noose and the stitches help us imagine a story.
