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When do you think a matching headstock does not look good?

I think certain types of non-Fender, old-school basses look best with a non-matching headstock veneered in rosewood or ebony, because it's the tradition. Would this be better with a koa headstock?

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Or this with a burst?

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There's a lot of "it depends" in this area, though, the very similar White Falcon bass looks better with a matching headstock than it would with a black one. And I'm not sure about this Rozeo...

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When do you think a matching headstock does not look good on a bass?
When I was too broke to look at nice basses, I looked at a lot of upscale basses with matching headstock, binding, big block inlays, etc. The thing that impressed me most was how basses like that in my price range were always without exception in really poor condition. Lots of burnt/chipped painted headstocks, loose, missing, and discolored binding, chunks of inlay, or an entire block missing, and paint in every stage of distress you can imagine. Not that I was ever attracted to bling, but seeing all those once nice looking basses looking like they were used to chop wood was enough to confirm my bias toward bells and whistles.
This was only fortified when I started tinkering with parts basses. I'd buy parts and assemble J basses. I quickly locked on to MIM bodies and necks as they were available, and while I got a few that were misrepresented by their seller, I never got one I couldn't make work. The rest depended on what I could find but I got to mess with bass assembly rather than joinery or any woodwork other than occasionally sanding a control cavity to allow better alignment of the guard and control plate joint.
 
Some colors just look bad with maple, and a matching headstock only makes it worse.

cherry burst is the strongest stomach turner for me, and it consistently fails to look good with any fingerboard, and looks the worst (to my eyes) with maple.

I do think that going fancy with matchy is cancelled out when you leave student dots on the face of the board. If there’s dots, there’s no point in the the body paint being anything other than brush-applied Model T Black, and no point in the headstock having any paint.
 
Depends on the colours for me. My basses don't except for the BB734 which is all black, the bass I built has an ebony headstock to match the fretboard and on my guitar I made the headstock to match the pickguard, both I think turned out great!

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I never cared much for sunburst matching headstocks, especially with Maple fingerboards. Solid colors, or a black headstock with another solid color can be ok. I have a black sb-2 with an ebony fingerboard ( that I have listed in the classifieds...wink, wink) that I really wish had a black headstock. Its maple, but I think a black hs on that bass would be Bada$$.