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My take: I think on the examples above, with the white "440" callouts on the hood or "Plymouth" decal on the quarter, or maybe a white vinyl top, white letters out would work very nicely. That said, I'm not a fan of white letter tires...blackwalls out for me.
White letters out is era correct for that car, and look fine to me. Generally, I don't like RWL, especially on early '60's cars. I have used Radial T/A's on my everyday cars in the past, but always black side out. Just my preference.