I'd suspect 50's to late 60's. Very possible the "69" patch is the graduation year. I agree with cpmac, the label does have a 50's look to it but these companies that made letter sweaters and jackets didn't really re-fresh their labels as often as mainstream labels like Arrow, Gant, and the various department store labels. The "Dry Clean Only" text also has me guessing a little later (late 50's or 60's).
9/9/14 at 5:35pm