This one needs some research. I'm not familiar with Sears's Economy branded patterns. For those of us who grew up with the big Sears catalog and their three grades of "good," "better," and "best," this looks like it might be their "good" line. I also know next to nothing about the evolution of men's undergarments, so I can't put a date to this one, though if forced, I'd date this one fairly early - 1900 to 1910, perhaps. These garments would probably have been made out of lawn for summer and flannel for winter.
Most of my early sewing books give extensive directions on making women's underclothes. making the argument that making one's underclothes is economical and that the choice of decoration gives a woman some area for creative expression. For men's underclothes, the only incentive would seem to be economy and it's hard for me to imagine a household in which making mens underclothes would be a necessity. As I said, more research is required.