I have to agree, time-wise, this one is difficult, however being a watch collector, I can tell you that the wrist watch was popular from around 1938 to 1946.
However, that still does not pinpoint the date either.
My grandsons are MATHLETES so they should really enjoy this one!

It would be difficult to judge the date of this photo by looking at the drafting tools. The same tools used during the depression were still fine to use into the late 1970's. Then, with the advent of CAD, suddenly we drafting teachers had to find money to fund the latest version of the software, and increasingly better computers to run the software. The drafting board, T-square, and triangles really do take me back to a simpler, and often happier, time.

Usually I'm pretty good at guessing the approximate date of a photo (within a year or two), based on clothing and hair styles, cars, and other background info. But this photo seems particularly timeless to me -- it could have been taken anytime between the early 1940s and the early to mid-'60s. (Or possibly even later than that during times when boys wore their hair very short, and wore classic, preppy clothes.)

Glad to see there was at least one girl in this mechanical drawing class!