Ah, the halcyon days at an all-male prep school, mid-century. Here we have two future lawyers shining their shoes while debating the merits of the various Ivies. The Hill School in Pottstown, PA, 1942.
Argyle socks and cuffed flannels:
Pants so short they go up to your knees when you cross your legs. The Hotchkiss School in Lakeville, Connecticut, 1954:
Wrinkled chinos, ties under crewnecks, light socks and loafers:
Rep tie, signet ring, freckles:
Breaking in the new teacher.
Finally, Steve McQueen visiting his old dorm room at the Boys Republic School in Chino Hills, CA, 1963: