I hope I haven't offended you with one or two comments about shoes over recent weeks. Aside from my obvious ranting about not liking socklessness with suits (or in general, much), I suspect that I might be one of those who's said "get better shoes" without adding something more helpful. I do generally try to be constructive, so I apologise if I have failed to be.
OK, I don't like the two-tone shirt, the almost-matching jacket and trews (although if they were matching, it's nice!), buttonhole doo-dah's, socklessness or boat shoes. But that's all so predictable. And also, you're clearly a guy who's pretty comfortable in his own skin and has some presence and personality, and I bet out in the real world of non-style-blog-reading humans, people tell you every day that you look awesome. Amazing as it might seem to some, I can relate!
So, constructive: you're right that if there's one place for sockless boat shoes, it's on a boat. And SB's right that if they were in better shape, it would make a difference. Maybe it's because I like shoes a lot, that I sometimes feel it's an oversight to add shoes to an outfit as a secondary item.* Anyway, in your case it's like this: shape. Whether they're cheap or expensive, country-casual or city-formal, shoes need to have some structure and shape to look good. Whether and what socks you wear, how you combine colours and whatever, are different issues but the form is fundamental. A well constructed shoe with an elegant last shape to me is the crowning glory of classic men's dress.
There are so many threads on this side of the forum about shoes, either brands, affiliates or just more fun threads like this. And this. So take a look, maybe, at this for inspiration. And price-wise, you could go anywhere from this up to this. Styleforum very much loves this. But let me take a leap here: you seem to like a striking style, and your shoes are mostly on the heavier side. Which is cool. Therefore, I'd suggest your true shoe love might lie here. Go crazy. Hope it works out. :)
*It actually offends me when a web site lists shoes under "accessories" instead of in their own category. I know, that's kind of tragic but whatever, we all have our failings!