I've said for a long time (although not here) that almost all of fashion appears to just be choosing a specific way to look, and honing it well enough to communicate you chose to look that way. Admittedly, it's possible this is overly dismissive of "true fashion" – for instance, the best applied makeup is relatively subtle and signals little (it's supposed to just be your face), except, it presents a better face.
I'm not sure where lines are drawn here. What's signalling and what's not? Bed head and such were fashionable for a long time, but only when paired with other clothes that might signal a carefully crafted signal of ambivalence. Hipster style seems to want to scream "I don't care, I just got cheap random stuff" – both of these are still signalling and make the best impression when they are ostentatiously intentional. But they can look a lot like the true, non-signalling appeal you might be on the lookout for, if you're me, and trying to correct their own misconceptions.
So the thing I started thinking about is a 2x2 grid. On one side, something being intentional, and on the other, whether it looks intentional or not. Then we see, in fashion, a gap – people never slyly try to look truly accidental. The closest I can think of is Rita from Arrested Development season 3, saying they should wear clothes inside out, and the horror from Lindsay when she discovers Rita's mentally handicapped. No one wants to appear careless – that's a vice – even if they will spend quite some time crafting the image that they're carefree.
I'm a computer programmer by trade (and, I admit, hobby, it's quite fun once you get good), I'm keenly aware of how people imagine suit-wearing programmers. It signals very negatively, of course. But I saw a speech at a technical conference by someone from a Fortune 500 company, where he briefly disclaimed his employer asks all employees to wear formal clothes when representing the company – and then gave a contemplative, memorable and deeply technical talk. And did so while looking pretty good – not the forgetful t-shirts or button-ups of the rest of the attendees.
It's worth saying that story has all the parts I'm interested in – the suit-as-ugly undertone, the disclaiming of the signal explicitly, the precision of presentation, and then the reversal. Because the ultimate signal is overcoming a minor negative prejudice. He knew what he had to say was strong enough to overcome the pre-judgment, and when that's true, you get a lot of deliberateness/confidence points in doing it.
But at the end of the day, did the suit have to also look good? I think the answer is, it couldn't look bad. Just leap over the floor of bad taste, and then appeal to people's actual values. Use the clothes to highlight your strength by not relying on them at all. With that in mind, I think I have a lot more respect for fashion than I did a year ago.