Read My Clothes

To judge from the names on the t-shirts and shorts I wear when out running, you would think I’d managed to cram attendance at several prep schools and a couple of Ivy League colleges into my formative years. Also, you might have the impression that when I was at Princeton I played lacrosse as I had done throughout my time at Choate (or was it Groton?), but when I transferred to Yale, my sport shifted to hockey. Go Bulldogs!

Now there is a fairly innocent reason for this misleading impression: I am not so much Ivy as Junior League material. That is, my budget-conscious wife picks up a lot of athletic wear for me at thrift shops run by this latter league. There guys named Chip who really did play lacrosse at institutions like Choate and Princeton tirelessly donate their clothes so that posers like me can run around pretending we did. This is a charity you won’t find written up in anyone’s social diary, a sharing of prestige that is all the more admirable for being anonymous. But don’t think we posers aren’t grateful!

Of course, my eclectic running wardrobe could also suggest that, like J.D. Salinger's Holden Caulfield and countless real-life ne’er-do-wells, I was kicked out of a series of fancy schools. “What? Did you blow up the library in the other two?” an acquaintance who noticed me sporting the insignia of my third school in a single week once interrupted my run to ask me.

“Worse. I set fire to the stables. But that’s how I got such glowing recommendations for this one. Didn’t you know that in prep school the more you screw up, the more people want to help you move on?”

In fact, this is a time-honored principle in the corporate world as well and thus an important way in which prep school does prepare you for this world.

But the real question is whether, on the strength of my shorts and t-shirts, I could actually be considered a preppy. Granted, such pretensions to preppiness might have been easily dismissed back in 1980 when Lisa Birnbach’s “The Preppy Handbook” was published. At least nowhere in the men’s clothing section of this book have I been able to find an entry for “castoffs.” But in Birnbach’s recession-era “True Prep” I did find such an entry. Only it was called “vintage,” and I was pleased to see that the thrift shop near where I live in New Jersey had made her “country-wide listing of great places to check out to incorporate vintage looks with your basic uniform.” I was also encouraged by a an interview with Birnbach (“Ivy Style” April, 2010), where she suggested that, as far as being preppy goes, what someone is wearing may not be so important as their having a proper “attitude of disregard” toward it.

If this is the case, my athletic wear comes out way ahead of a pair of taped together loafers. I am like a canvas onto which various school colors have been flung with reckless abandon, a billboard advertising competing brands all at once or at least in close succession.

The irony is that there is only one place I could have learned to dress with such disregard, and that is prep school. Yes, beneath all my posing, I am something of the real deal, having spent several Salinger-esque years at a Washington, DC Episcopal school for boys, though I never played lacrosse or blew up anything. At this school, with its strict dress code, future captains of industry and large government bureaucracies grew comfortable in the attire destined for them. They did this by wearing their mandatory ties flung over their shoulders and their mandatory suit jackets often not at all as they scuffed their loafers against all manner of surfaces, including desk tops, fellow classmates, and on one notable occasion the roof of the science building.

The lesson I took from all this was that no one is too young or immature to don the uniform of a social caste. Now for a while I worried that my own kids might not figure this out in public school, but my fears turned out to be groundless. On a recent trip to DC, I was pleased to watch what happened when a cute blonde woman wearing a colorful Lilly Pulitzer dress and clearly bound for Georgetown or Capitol Hill sat down next to my 6-year-old son on a bus.

After giving his t-shirt a mischievous once-over(I am not the only one for whom my wife scouts Junior League shops), she asked, “Do you go to Princeton?” Without even so much as pausing to consider whether she might be out of his league, he flirted right back at her with a smile that seemed to say, “Princeton? Sure. Class of 2025.”

A “chip” off the old block.