Those are some cool wheels...
It is always hard saying what would look good for someone else. Personally I like the tire to fill out a fender well. It is cool having a taller tire in the rear. And with the truck having about a 3" rake. But take into consideration that I was a teenager starting to work on cars in the late 60's. Having the rear end jacked up was the style.
Over the past 50 years tastes have certainly changed, so it is all about what you like. If your preference is having the tires about the same height, then I can respect that and bet it will be pretty cool. Here is a link to one of many tire size calculators -
https://www.tacomaworld.com/tirecalc...0r20-255-45r20 With the 295's, looking from the rear, it will be a good amount of meat on the road. That never looks bad...
I do have to ask, with your wheels, do you know the back space? On my 9" wheels, there is a 4.75" backspace and the 275/60/20 fit in under the wheel well very close to the outside (<1"). On the front 275/45/20's that is also close but maybe about 1.5" For the rear, I would think that you would need at least a 5.75" back space, unless you want the tire to stick out past the fender.
Hope the pictures come across, think that I finally figured it out...