This mischievous boy wearing a striped T, rolled up denim, and high-tops comes to us all the way from 1963. His jeans are Lee Riders.
Lee has out-smarted boyhood by making Lee Riders really rugged. That tapered cut prevents baggy knees.
A similar ad appeared in the fall as the back-to-school season approached. Here an older boy is wearing the same jeans. This one is sporting a tie, sweater, white socks, and shiny black loafer. How mid-century spiffy is he?
A modern-day version of classic rolled up Lee Riders is found on lee.com. The 2022 men’s (no luck finding a similar look in boys denim) version is styled with boots and no belt. You can see the classic denim selvedge on the rolled up version. The 1963 version is a surged seam. Both versions show off the leather patch that brands it as Lee.
Mid-Century Page 
That brings back memories.
LikeLiked by 1 person