I have a guy I work with from time to time who is a huge SW&D type dude. He's told me he's on the forum, but won't say which name (he's also on SUFU and SZ). Needless to say he has quite the penchant for clothes that make a "statement." Generally he's either completely in white or completely in black. It's quite humorous when we meet for a project. Like living both sides of the forum.
All that said I think he has, arguably, the most refined personal style of anyone I know. Not only does he never stray from the expected (knocking out the uniform portion of the style equation), but he always has a personal spin here and there that keeps things interesting. Granted, I know next to nothing about the more avant-garde realms of SW&D, but I do notice his attention to detail and insistence on what is his idea of a perfect fit for this clothes.
While I doubt 99% of the people he comes into contact with look any deeper than "that dude is dressed like a weirdo," I think it's important to remember that we all have our own things that we harp on and obsess over. So long as someone takes getting dressed seriously and finds an identity in their clothing, I say all the power to them.
Just as no one will ever understand why we wait a year and a half for an overcoat that we travel to Italy to get fitted for, we can't really judge someone on what they think is appropriate or cool. So long as the due diligence is done and the understanding is there, then the objective part of "style" is undeniably present. The rest is far too subjective to attempt to classify or trace.