Hi there. Troll here.
Good to see that the takeaway isn't at all what I intended to communicate. I will take greater care in the future.
CBD isn't my MO. If you find yourself there, then I think you'd get more help from someone else.
As for the discussion at hand:
Here I am wearing navy cords and lighter/chili shoes. Put up or shut up for me if you will. Spoilered as the shoes aren't AE. Warning: Spoiler! (Click to show)
Shoes themselves have a low abomination level. They are very consistently country casual. Pebble leather, boot, blucher etc. This fact makes it easier to get away with a less than traditional combination because my outfit doesn't have to fight with the shoes.
Light shoes with dark pants is visually jarring and light shoes are casual. Therefore I needed to pair them with similarly casual items. Navy cords fit right into the country casual realm. Though they provide a strong contrast, so I will need to be careful with the rest of my choices. A matching navy tie is sedate and simple for the top block, however note it's styling. Sticking with the country casual theme we have chosen forces me to take a square bottomed wool knit. A silk tie wouldn't have worked nearly as well here. The jacket needs to be light to contrast well with the pants, and it needs to echo the country casual theme as well. Light gray flannel is a perfect choice. Shirt is similarly consistent as it is an OCBD, although the stripes might be construed as more "city" by some and may be discordant. A standard light blue OCBD may have been better.
My main point is that when you break rules, you need to do so knowledgeably with all other aspects of the outfit on point or you will look bad. Additionally, some rules are harder to break well than others.
Light shoes with a navy suit attempts to mix a very formal/businessy upper block with a casual shoe and nearly always looks jarring and discordant. This is even worse if the suit is very worsted or pinstriped etc. I maintain that is extremely difficult if not impossible to do this well, and if you just slap "country" pebble LWB on while you are wearing your worsted navy suit you aren't "rocking" it. You are just okay with looking bad.
I don't want people to "conform", I want people to execute their personal style WELL, and it takes knowledge to do that. The "rules" should serve as a guide and should certainly be broken. However, the only way to do that in a genuinely stylish way is to take the time to learn the rules and WHY they are what they are. If one simply says "I don't care about the rules" from the outset, then they are doomed. Sometimes they will put together something stylish, but it will have been an "accident" if you will and they won't be able to dress sharp consistently.
I have little style and do not know the rules..I simply apply my former artist training to what I feel matches and does not match and I am very fine with it....that being said I enjoy your explanations of the rules and how you come about putting your clothes together. Well done!