"The Forum Wars"
I don't think you should sell the funky stuff. I think it looks just as good on you and frankly, slightly less contrived. I'm getting the sense you're having issues about what's age-appropriate? Or am I just projecting?!
What isn't being talked about here is context or lifestyle. If everyone is going around in sportsjackets, waistcoats and poetic scarves, I would go the other way.
Maybe you need to combine these two looks? Is it possible? Why either/or? How about the drop-crotch pants with the white shirt? Untucked and open-necked.
Thanks for posting,