Dating vintage Florsheim shoes?

[pdxvintagette]

I acquired today two pairs of vintage Florsheims and one similar pair from another brand. These were obviously well-stored and taken care of. Unfortunately, he wore them enough that the front leather and heel have been replaced in the past (NOT recently ... Goodyear Neolite heels). One pair of black wingtips and two pairs of casual dress shoes. They don't LOOK well enough worn for this to be done, but there it is.

Is there a way I can date these by the appearance of the "The Florsheim Shoe" label, and other interior markings?

I'm leaning towards late 30's, but as these will be sold, I am concerned about dating them correctly.

 

[Tomasso]

Pix will help.

 

[WildCelt]

How about this pair?
I got these at a thrift store the other day. I'd love to know their general age, but I haven't the first idea where to start.

 

[carouselvic]

little known fact

Statistics show that 9 out of 10 guys dating Florsheim shoes still prefer women.