I get this Q all the time, and the answer is you can; just not from a dealer show room. There are plenty of independent shops who can rebuild a 53 Pontiac or whatever with all the modern conveniences, even as EVs.
https://twitter.com/al_mutaghatris/status/1382330582412128259
And the reason car manufacturers don't do it is because it would be 100% illegal, crash safety regulation wise. Same reason most all Detroit retro designs are ultimately disappointing (at best).
I dig Jaguar's C-type / D-type / XKSS continuations. They had unused 1950s VINs for the originals, which (in the UK anyway) allowed them to make brand new replicas. Don't expect A/C & GPS, and if you have to ask the price you can't afford it.
jaguar.com/about-jaguar/j….
jaguar.com/about-jaguar/j….
No legal barrier to upgrading an existing old car with new tech though. My friend Jorge Zaragosa's 55 Chevy Nomad is a neat example; LS7, fully independent suspension, modern A/C & power equipment, GPS, etc. 
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