2-5. Tasteful, classic designs, but do they fit? Instep looks a little low for you from this angle (same for me with some US shoes) and the last shape might not be ideal for you.
6. Not bad, but again, fitting properly? Down one size, up one width perhaps.
7. Hard to tell; classic style, why do they look so loose around the heel?
8. Meh. Conceptually nice, but look as cheap as you say they were.
9. For teenaged girls, or at a push, jeans and dim light.
10. Shapeless AND horrible.
11. Robustly horrible.
12, 13. See 9
15, 16. Rather nice from this angle, and the kind of thing I think others suggested as consistent with your style (not PB, obviously, but until you've five black captoes side by side, he can never love you).
17, 18. Disposable.
19-22. Pop the Zippo, call a priest.
You're in the City. I suggest getting measured up at Allen Edmonds or similar. I suspect, like a lot of people, you are up-sizing a lot instead of going up a width. Your heel shape might also be causing you some fit issues - but only you know. With a bit of ammunition on your size and experimenting with some sizes and last shapes, I think you'll be in a better position. Actually, as someone failry new to AE myself, I find them quite helpful: they have seemingly infinite size variations and a few different lasts, so it seems a good place to experiment, and a well-known starting point for subsequent reference ("I'm a 10E in AE 5 last, what size in....?" etc).
Sharper loafers are already in your locker by the look of it, as are some classic dress shoes. Put some investigation into what really fits you. Maybe if you like things a bit more casual, try some dress styles in suede, also a chukka and a monk. There's a whole world of joy out there.