When is 'character' over clinical sharpness the right call?

Hey everyone, Derek here, 1st AC. I've been wrestling with a concept that keeps popping up: the idea that maximum sharpness isn't always the goal. I get the theory, but I'm trying to wrap my head around practical narrative examples.

Recently, on a short film shot with an ALEXA Mini, we had some vintage glass alongside our modern Cooke primes. The director kept leaning towards the older lenses for specific moments, even if they weren't as 'perfect' as the Cookes. It made me wonder about intentional choices.

Beyond just 'dream sequences,' what are some specific narrative scenarios where a lens with softer rendering, interesting bokeh, or pleasing flares would genuinely be a more powerful or impactful choice than a technically pristine, sharp lens? I'm curious about the specific 'why' behind those decisions.