Prep Rally

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:

7 Comments on "Prep Rally"

  1. Lagerfeld Forever | December 8, 2008 at 1:19 pm |

    Excellent. I live right up the road from the Boy’s Republic in Chino Hills. They don’t dress like that anymore, unfortunately. I didn’t know Steve McQueen was a resident, either.

  2. yeah boys republic isn’t exactly a prep school. it’s more like where you get sent as a teenager as your last chance before being turned over to the penal system. but it’s true, steve mcqueen was an alum!

  3. The student sitting directly in front of the teacher, underneath the caption “Wrinkled chinos, ties under crewnecks, light socks and loafers” is DEFINITELY not thinking about the lecture!

  4. The Hill School still remains one of the most ivy-influenced school today. It is still very traditional- practically identical to “Dead Poets Society” except with girls now. Nantucket Reds and Brooks Brothers oxfords can be seen left and right.

  5. Christian | July 29, 2011 at 2:45 pm |

    Do you work there? Alumnus? Live nearby? Why not do a story for us.

  6. I’m a student there. Livin’ in the glorious days of good ol’ prep school. 🙂

  7. Bill Quick | April 24, 2016 at 9:10 pm |

    I’m Hill School class of 1964. Tobias Wolff was one of my classmates. Looking at those pics, and from what I saw of Upper School when last I visited a couple of years ago, it doesn’t appear that there has been an enormous amount of change. That freckled, signet-ring kid is wearing a Hill School tie, right? Sure looks like it.

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