I'll start with the easier of the two jackets to identify. Those ribbons usually give a good rough estimate to begin with, and in this case the yellow ribbon (partially cut off in this pic) is the Asia Pacific Medal ribbon, given to those who served in the Pacific Theatre during 1941-1945. The red ribbon is for the Bronze Star. This award was awarded to any service member, starting on Dec. 7, 1941 (Pearl Harbor), who display heroism or merit in service. So it is very possible this jacket is from the late 1930's, and 1945 at the latest.
Never ceases to amaze me. Thank you!