The photo from Wikimedia Commons has a caption that reads: "October 11, 1941 University of Michigan versus the University of Pittsburgh football game program. The Board published it in Control of Physical Education at the University of Michigan."
The leather design in 1941 has the distinct pattern that we still recognize even though no face mask was equipped fo the soft material design. Note the brilliance of the winged design that carries over to the modern day helmet design of the Blue and Maize.