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.
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.