LabelKing developed massively during the time he was on here, even though he always had a certain eye for the flamboyant. Tirailleur has certainly changed in a very positive way too. I haven't been paying so much attention to AAS (sorry!) so I can't say. And look at Spoo and In Stitches... Almost all the people here who have stye worthy of emulation have come a long way from where they started.
I mention those three as they do their own thing ("rock" it, if you will), but they do it well. RTC probably has no interest in dressing like I do (with 6 going on 7 blue blazers), but giving those three as examples demonstrates that there is a way to break the rules and look good...and therefore must also be a way to break the rules and look not good. There is a way to "rock it" properly. And it takes far more work than dressing like I do. For example, I don't always like AAS' fits, but I'm always impressed by them.
I suspect he's very well aware. One of the benefits of consistently dressing well is getting the benefit of the doubt. Breaking rules with intent rather than out of ignorance. Whether or not it looks good is a different matter...
...though in this case, I dig it. Wouldn't wear it. But I dig it.