Do you know your "friends" hat size?
Have you seen him wearing the style you have in mind, or do you "just think this one will look good on him"?
His taste and your taste may not be the same taste, he might prefer a fedora after all.
I know the "GROUP THINK" here is you don't need black shoes, but
When I wore suits daily I wore more black shoes than brown and still have more black than brown dress shoes.
Though I agree that I would not buy any shoes in the OP's examples.
"No. That’s a false analogy. Loops without a belt looks like you didn’t finish dressing yourself, an entirely different effect."
This should be the final word
But I have a feeling the OP will have different idea.