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 (click image to see clothes and pimples in hi-res):

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: