Have you ever wondered why the older Florsheims used the heavily nailed heels on the double soled wingtips? One big reason was because those gunboats used a solid piece of plastic directly under the top part of the heal. In order to make the leather top part stick on they needed to use lots of nails to attach it to the plastic heel. If you look at most Florsheim you will find the heel attached to be plastic! Underneath that plastic is the leather sole attached. Even the shoes made in the 1950's have this, and indeed some other 1950's gunboat manufacturers have plastic heels also. Florsheim for some strange reason wanted to cut costs on such a beautiful shoe, so they made the weird decision to use plastic in the major part of the heel, BUT they encountered a problem, that is...the top part of the heel would come unstuck, so they ended up using multiple nails in the heal to attach it solidly to the plastic underneath. Now, according to this article the Kenmoors that used this famous heel were first made in 1958, so what did the gunboat heels look like in the 1940's and before? Were they heavily nailed, and when did Florsheim first start using plastic in their heels? http://vcleat.com/florsheim-model-numbers-1950s-90s/ Of course you will see some gunboats with an all leather heel, but me thinks these were cobblers replacing the plastic heels with leather after a repair job was done. Many old pics do indeed show plastic heels. All my old Florsheim Imperial v cleat wingtips have plastic heels...they look like leather, but when studied carefully they are indeed plastic. The investigation continues.The theory is that those multiple nails solely exist to attach the top lift to the plastic so it can grip properly. There is lots of evidence to support this idea, and the only way to really dispute this idea is to find an NOS model that uses those multiple nails with a leather layered heel. I am really starting to think that those multiple nails exist solely for this reason, to make it easier to attach the top lift to the plastic heel.