How about playing with the aesthetic of 'unsophisticated' taste?
A deliberately unrefined form of Dandyism?

Heavy shoes which don't remotely aspire to elegance?
A certain pleasing coarseness of Tweed?
A 'rough' look?
Burly, even?

Nothing effete or sophisticated, but still planned, plotted and executed with care.

No cashmere or other 'luxury' fabrics, no obvious 'clothes-horse' touches, just... MENSwear?

Can it still be done without it becomming a form of 'Drag' or parody?

Are we now too far removed from the world when (we imagine) men 'just got dressed' and yet looked great?

I've been looking at old family photos this PM and remembering some of the men pictured. They look good to me now. Back then they were just... ordinary. I imagine they 'just got dressed', maybe I'm kidding myself. I have no way of knowing what they thought about their wardrobes, or even if they thought much about them at all. I just like their look, that's all.

Strike a chord with anyone?

David.