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The Beauty of Feckless Prep School Youth. A High WASP Style Archetype.

Feckless is a Scottish word. Many meanings. One of them is irresponsible. That’s what I’m after. Irresponsible as only those who don’t yet know how fortunate they are can be. The prep school boy is perhaps the best known of all High WASP style archetypes. He throws his clothes on, always in a hurry, in a hurry to lounge somewhere, not a care in the world, or to lope casually across a campus, lanky, endearingly clumsy with a shy sort of gait, apparently graced with all the world has to offer. It’s all an accident, of birth and fortune.

His clothes are almost always too big. Or too small. His arms too long for his shirt sleeves, hair on his wrist catches the light. Unbuttoned cuffs expose his father’s old watch. His mom bought the blue blazer and guileless tie last year for the junior prom. Before he grew another 3 inches. He has pulled open the knot of the tie. Wears his older brother’s baggy khakis. A pair of white squash shoes, because, you see, he was in fact playing squash just an hour ago. Before he felt compelled to sit, just there, in the afternoon sun, face turned to the sky, lashes on his cheek.

Before he felt compelled to sit, just there, on the bench at the train station, waiting to go back to school. Cheeks flushed. Skin a little chapped. He’s an object of desire.

Many different sub-groups revisit this archetype. Below, from the New York Magazine Home Design section, via WASP 101, and again on Monograms and Manicures, a boy who has known all his life he want to be an interior designer. His style of choice? Feckless Prep School Youth. But studied. Mannered.

We must know that the real version is apt to cover his walls in irreverent pictures of one sort or another. Strew shin guards and socks across the floor.

For those attempting to recreate the Feckless Youth in traditional adulthood, there is, of course, the Mogul of Feckless. Ralph Lauren, born – as we all know – Ralph Lifshitz. More power to him. No dummy he. He understood that the young man in the sunlight captured the American imagination like no other. Except perhaps the cowboy on a horse. Lauren has made a fortune from his understanding.

Modern classicists have a more subversive evolution of the style. secret forts, one of my absolute favorite blogs for men’s style, highlights a collection from Apolis and ties from C. Chauchat.

These ties are anything but guileless. However, they refer, in a sort of post-modern way, to the ties you find in the bottom of your backpack, and throw on as you leave in a rush after some indeterminate athletic pursuit. Which most likely involved sunlight, slashing golden across fields.

The thing is, the real boy doesn’t try. He doesn’t know the effect he has on everyone. His anxieties are elsewhere, waiting to make him write A Separate Peace. The minute you try to dress like the Feckless Prep School Youth, he’s lost. He’s mythologized. But that’s OK. We are a country of myths, after all. Go ahead. Dress like him. Recreate that object of desire. Focus on looking like you didn’t try, even if you did. You will get close enough for your purposes.

You might ask, with good cause, does the Youth exist? This I know. He did in 1977. I saw him once. (I have told this story before, I am sure, but give me the consideration you give an older relative who has begun to repeat themselves. If you would be so kind.)

In the fall of 1977 I turned 21. My two best friends at Princeton kidnapped me, and drove me to New York City in a BMW 2002tii. Remember those? I didn’t know where we were going. It would turn out to be the Plaza Hotel for a night. But as we crossed town, waiting at a stop sign on the East Side, we saw a boy on the sidewalk. He was wearing khakis, a blue blazer, a tie. Carried a large bouquet of flowers. Hair just so, short on the sides, longer and tousled on top. The wind of late September blowing. We said to each other, my friend and I, “Oh look at that boy. How adorable.” We thought perhaps his flowers were for his mother.

In the middle of the crosswalk, he turned, and walked around our car to where I sat in the passenger seat. “Hello,” he said, politely. Handed the flowers through the window. “Here. They were for my girlfriend, but she’s not there. Since you are so pretty, they are for you.” And off he sauntered.

So. He existed. Whether he is still out there anywhere as a boy, rather than a retailing construct, I don’t know. But he existed. Loosened tie and all. Made my damn day, even then.

Collage: Polyvore
Boys on bench, boy in dorm, WASP 101
Ralph Lauren; shirt, tie
secret forts

23 Responses

  1. What a great story! Better not to know where he ended up. Just keep him young and perfect forever…

  2. your description of the schoolboys at the train station is exactly what makes me swoon for rowerboys- my heart is pitter patting!



  3. A Separate Peace vs. The Catcher in the Rye… I still cannot decide which one "spoke" more to me in my youth.

    Your encounter with this boy? That felt to me so like something Ryan O'Neal's character from "Love Story" might do. :)

  4. Ahhh. I went to prep school in the east coast of Canada, but we did not have classic prep school boys there. Those I had to wait for till I came to America.

  5. Oh yes, they existed. Probably still do, but the ones I especially remember filled the high school section of where I went to middle school, and the high school where I went in your college town. I still have some photo prints that were castoffs from the yearbook, where one can observe the Oxford cloth shirts and khakis and such…which is of course what my BF lived in (well, when he wasn't wearing a softball shirt).

  6. Thank you so much for sharing that story. What a lovely way to begin my day and what a lovely remembrance for you!

  7. I love nothing more then a boy dressed up in khakis and a rumbled oxford, extra points if they have a pair of scuffed up bucks on thier feet!

  8. A boy with the capacity for the spontaneous romantic gesture- don't you wonder what became of him?

    There is the girl counterpart, often a polo short over a careless khakis or skirt, shins scored from field hockey.

    I knew boys like that in the 60s, some wore shetland sweaters, usually inside out. Topsider sneakers or Weejuns.

  9. How charming!

    Mr Magnolia laughs that the way to my heart is through dressing like a Bond Street barrister. I will admit that braces make my stomach flutter…

  10. Well done. Mine's name was Jamie, he is still out there, with that look, in Annapolis. i have always thought he, all by himself, would make a fabulous American museum…

    And of course, this begs another post, "Best pick up lines" :)

  11. Love that story – keep him in your heart for always…..
    And yes, those boys exist still in real life – I see them in the town of Marlborough, Wiltshire, UK when I go and get my groceries…(when I am back living in England)…. They are very lucky boys who go to Marlborough College there – one of the best schools (and probably one of the most expensive too) in England….- they probably a. dont realise how lucky they are and b. that they are 'these' boys either!! But they make me happy!

  12. love this post. reminds me of boarding school days:) ah pink pants… why oh why do men still think they are cool and high society??? lol…. hilarious, but also fairly comforting whenever I see them in a place outside the obvious. does that make sense? something tell me it will to you!
    thanks for the lovely writing

  13. The boy in the dorm!!!
    That boy graduated from my college last year! I recognized the picture from our school magazine as they did a feature on him.
    Every day my friends and I would love to see what he would be wearing.At the gym? Ralph Lauren white tee shirt.Amazing.

    Everything he did and everything he wore was just the best!

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