Wes Sullivan grew up in the great depression, and times were tight. He talked about how the family would splurge once a week by buying a Coke and a five-cent candy bar that everyone would share. Still, this picture is obviously a dress-up activity.
Styles change, and boys now wouldn't be caught wearing a frilly collar or high-top, lace-up leather shoes with leather soles.
Wes with his cousin, Jewel, and they appear to be examining a passport.