In order to determine the age of your Red Wing 2268's, one should first be familiar with their tags. This will provide a good indication of the time frame in which the boots were produced.
In the 1930's, the railway transport system was a vital necessity for America, and Red Wing created the 2268 Engineer to support the feet of the railway engineers. This Red Wing boot protected the feet of the engineer while also protecting their feet from the steam of the fires within the locomotive engines. Red Wing Engineer Boots made their first catalog appearance in 1938.
Photo from Red Wing Shoes
1940's / 1950's Needle Loomed Tag
Founded in 1918, the American National Standards Institute (ANSI) is a private, non-profit membership organization that oversees the development of voluntary consensus standards for products, services, processes, systems, and personnel in the United States. The ANSI standard incorporates a coding system that manufacturers use to identify the portions of the standard with which the footwear complies. The identification code must be legible (printed, stamped, stitched, etc.) on one shoe of each pair of protective footwear.
Below are the tags many of us are familiar with. Of all the numbers on this tag, one should take note of the two following "PT."
Line #1: ANSI Z41 PT83:
This line identifies the ANSI standard. The letters PT indicate the Protective Toe section of the standard. This is followed by the last two digits of the year of the standard with which the footwear meets compliance (1983).
Line #2: M I/75 C/75:
This line identifies the applicable gender [M (Male) or F (Female)] for which the footwear is intended. It also identifies the existence of impact resistance (I), the impact resistance rating (75, 50 or 30 foot-pounds), compression resistance (C) and the compression resistance rating (75, 50 or 30 which correlates to 2500 pounds, 1750 pounds, and 1000 pounds of compression, respectively).
PT83: Made from 1983 through 1991. The vertical tag and toe tracks are usually indicative of early 1980's models. This model is more desireable in the Japanese market and the vertical tag can bring in at least an extra $50 to $100 over the PT91's and 99's.
PT99: Made from 1999 through 2005
As of 2005, American Society for Testing and Materials (ASTM) F2413 standard superseded the ANSI Z41 standard. Unfortunately, the 2268's have been replaced by the not-so-appealing new line of Red Wing Engineer Boots; however, the former are still being mass-produced in Japan.
Photo from Red Wing Shoes