This box contains the earliest version of the Esterbrook desk pens. Note the "Re-New-Point" reference and the different font used. The pen for this box has the full R. Esterbrook + Co. imprint with a solid black or solid red taper.
This box is for a bandless desk pen with a grooved spade style lever. It's a shorter box than the others.
This box I believe is for a standard clear taper desk pen. I don't have a pen in it, but the style looks similar to later models.
This box has a model W with black taper. Outfitted with original price band, $1.50 bought this for you back in the 1940's.