First off, the OP has earned a certain level of my respect for posting his pics. From what I've seen, he's received a lot of criticism and ridicule on this forum but he has never gotten upset and reacted badly and has "put his money where his mouth is" by responding to the requests to photos of his "style".
For myself, I've only recently started to make an effort to "dress properly". 6 months ago I had no clue that a suit needs to show 1/2" or so of sleeve, about pocket squares, I had way too much break in my pants, that square-toed shoes were awesome, etc.
I'm 28 years old and soon going to be entering a professional working environment once I get finished with grad school and I still have a way to go to define my own look. However, I do think that most of the OP's clothing choices are absolutely horrible. That first suit and the black platypus shoes (as they are being called) in particular. Oh, and those awful tie knots as well. I don't care about a dimple or not but those are huge and obnoxious and just look plain bad.
If he is happy with them, then so be it but I have a hard time thinking that even the "average Joe" (or Jane in this case) would find them appealing. And this is coming from someone who just spent Sat night at a lounge in Manhattan with a bunch of my classmates (all within +/- 4-5 years of my age) celebrating a friend's birthday; whose clothing consisted of square toed shoes, jeans with french cuffs, one "fashion coat" with tie halfway undone and one side of the shirt tucked in, and comments to me of "don't you ever wear jeans?" That's their accepted style yet I'm 99% positive that those same people would not dig this look either so it's not just me being snobby.