Warning: Spoiler! (Click to show)
GMM - I dont think the people you mentioned looked any better than you did in regards to the specific point of wearing a more structured rig together with calf loafers and no socks. If you were to go back and look, and this would be very tedious and time consuming, but it is something I have undoubtedly noticed, you would see that from the advent of the thumb system, many well respected members posted fits that got 15 thumbs, 10 thumbs, or less. And usually it was when they did something similar to what you did. An otherwise great fit, with some particular piece that stood out as off.
People may not have voiced it in posts, but you could always tell from the thumb count when a fit was found suspect. I would assume that when you have someone who has garnered a certain reputation, or has been around a long time, viewers just assume that the decisions they make are intentional, and while the viewer may not like it, they don't feel any use in pointing out the "error" as its just chalked up to, "thats how they roll." But who knows, maybe said SFer would have been like, huh, thats a good point, I shouldn't have paired those things together. We'll never know because no one said anything.
Other people don't get that space. And while at first that seems unfair, the truth is, its kind and beneficial. Would you rather post things that people find to be off and get no feedback? Just 8 or 11 thumbs and never find out why people are not connecting to your fit on a particular day? There is nothing better than getting feedback. No one is obliged to agree with every bit of feedback they receive, but at least it gives you something to think about, and it provides you with a clear understanding when and why something did not click for the viewers.
My advice would be to chuck the comparisons to other members out the window. When you get feedback or critique, instead of thinking about the last SF legend who got away with the same crime, think about why people are saying what they are saying. After that, you are welcome to agree with them, or politely disagree. I disagree with feedback plenty, and other times I see the point being made as more sensible than my opinion, and make changes because something is pointed out that I had not realized. The conclusion you come to is entirely up to you. But if you want to have the opportunity to at least have the chance of considering peoples feedback, you have to get the feedback to begin with. I think its much more valuable to have people honestly telling you what they think is good or bad, than to have people say nothing and just think to themselves, oh, I don't love that, but I best not say anything because thats just how that guy rolls.
Lastly, while the focus of that last fit shifted to the shoe choice, lets not forget that everyone agreed that outside of the shoes the rig was outstanding. Like, true top level achievement. Thats nothing to sneeze at.
My 2 cents anyways.
I could count on the fingers of one hand the number of feedbacks I've had that have been flat wrong.