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Matching headstock?

No. Never paint the headstock to match the body color. The neck is a continuous piece of wood, and the face of the headstock should match the back and sides. Sorry, one persons aesthetic opinion.

Practically speaking also, owning several Fender-style basses, I can swap necks between them at any time without being concerned about the headstock clashing, because it is woodgrain.

???????? I don't even know to respond to such insanity.
 
Here's my blue 6 string headstock:

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And my blue Yamaha trb5IIf mij 5string headstock
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Kia ora bass whānau!

I am in the process of refinishing my Squire PJ. It was a 3TSB going to a baby blue. Question is should I paint the headstock to match? It's got a rosewood board.
Also, pics of your matching-headstock basses are encouraged!

Ngā mihi nui! View attachment 2827193

No pics right now of my basses (posting from my phone), but for me a matching headstock looks good with a dark colored fingerboard (e.g., rosewood or ebony) but not so much with a maple fingerboard.
 
I love a matching headstock, especially on a burst finish. My first Stingray was a vintage sunburst with a matching headstock and it was beautiful. I'll have to dig up a picture when I get home from work.

I currently have a cherryburst L-2500 with a matching headstock and it, too, is beautiful! I also think the markerless fretboard eliminates some visual "distractions" so the headstock is a little more prominent.

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