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

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That sparkle burst J is GORGEOUS
 
Generally all the time. - There are some exceptions, but in general, I think the core wood should just be the color of the headstock.
Also, kinda on the subject, not a fan of blank headstocks from custom neck shops either. I think whoever the maker, should offer a factory applied logo decal as an option. Especially when it's an FSO headstock. Blank ones just look naked.

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Personally, I can't stand a matching headstock. I bought a MM Stingray 5 in a beautiful translucent yellow/gold color almost 20 years ago. It was a fantastic playing/sounding/and looking (aside from the headstock) instrument. I loved it, but I loathed looking at the headstock. Eventually, it bothered me so much I sold it.

I've come to realize that as shallow as it sounds, a matching headstock is a deal breaker for me. Go figure.
 
Old timer here.
Back in the early 60’s painted or matching headstock signifies a low end knockoff instrument.
So as a bass player who started back then I still think it makes the instrument look cheap.
Only the Beatle Bass pulls it off fairly well. IMVHO
Duke

For Fender in the 60's it was mostly reserved for their high end models; Jaguar, Jazzmaster, Jazz Bass and Bass VI. Same ones which further into the 60's got binding and then block markers as their 'deluxe' models. I think it still really works with those offset models in particular.
 
When do you think a matching headstock does not look good on a bass?

My old stand by. I spend a lot more time playing a bass than looking at it. When I’m playing it, I’m looking at the fingerboard not the headstock or any other part of it for that matter.

I will say that a Fender Jazz with block inlays on a dark rosewood finger board, in either Lake Placid Blue or a whatever that shade of green that’s been posted here the last year of so is pretty sharp looking. All else, meh.