These are family photos from my father's second wife. In the first photo, her father is either the kid on the bike, or the one at the back. He grew up in Texas, and was one of twelve siblings, only 9 of them were born when this photo was taken.( all 12 lived to adulthood) He became a Seabee in the Navy, and worked in an on ship post office in the Pacific during WW II. He later moved to Ponka City Oklahoma.
Nice catch..Lookin back they do look like rubber boots turned down. I remember kids with 6” cuffs…guess their moms thought they would grow into them.