Thanks for the input. Here’s another shot with the door trim shortened a bit.
The 59 Caddy tail light mounts are machined out of aluminum and then powder coated. They are shaped to resemble the profile of the stepside fender. The assembly bolts to the stake pocket, and can only be installed or removed with the fenders off. It’s comprised of two pieces, the part that bolts to the stake pocket, and the piece that contains the lens housings. They are held together with socket head cap screws between the lenses. The mounts are more complicated than I originally designed, but my son is a machinist so he added the extra touches that conceal the attaching hardware and wires. There’s a recessed cavity inside, and the wires run through the bracket into the bed wall and are connected under the bed.
Here are a few pics showing the pieces and the finished install:

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Here’s the back side of the lens section which fits inside the mounting bracket, which in turn bolts to the truck.
And here it is bolted to the truck before the fender went on:
They attract a lot of attention at night:
I also thought about mounting the lights directly to the fenders using something like 1962 Plymouth tail light bezels, but I really wanted them side by side. I actually wanted 3 per side, to allow sequential turn signals, but it just doesn’t work on a truck like this.