For the latest installment in Ivy-Style’s series of reminiscences and anecdotes, the blogger known as Longwing spins a tale about a trip to Nantucket in his love-struck youth, and its effect on his sartorial tastes.

In the summer of 1979 I traveled from my home in Louisiana to visit a girlfriend who was summering in Nantucket. She was working as someone’s nanny and sharing a home with about 20 similarly employed youths. The girlfriend thing turned out to be a disappointment, but Nantucket was something to remember.

I had learned the prep look in New Orleans, where it was known to the locals as Uptown and on campus as preppy. Up to that point the look meant little more to me than welcome relief from the “Saturday Night Fever”-inspired styles of my early high school years. My own beginner’s wardrobe was quite simple: I spent 90 percent of my time in khakis, an oxford (usually in need of laundering), and Top-Siders. Many of my friends had clothing that showed true devotion to the style, but I’m not sure I even noticed. And getting my sober ass down to Perlis to stock up on the goods was not a high priority.

The trip to Nantucket changed all that. The so-called girlfriend was working days, so I had plenty of time to look around the island, and I liked what I saw. I liked the red pants. I bought some. I liked the way everyone looked like they had just gotten off their sailboat. My friends in New Orleans were more likely to look like they had just returned from a fishing trip, which is fine, but didn’t capture my imagination in quite the same way.

Even though the signs had always been there, I needed to break away from my limited view of campus and fraternity life to understand that the look was more than I knew.

The following spring I made my way to Louisville for Kentucky Derby, where I would once again experience the style in a potent form. Only after experiencing Nantucket and Louisville did I begin to understand that there was much more to this look that I had so casually and carelessly co-opted.

I’ve never been back to Nantucket, though I wouldn’t pass up the chance to go again. I’d be very surprised if it were anything like I remember. It was quaint in a way that is hard to imagine now.

And honestly, I’m not sure I want my memories tampered with anyway. — LONGWING

Our latest Old Yarn, Ivy-Style’s new series of anecdotes and reminiscences, was submitted by Chris Hogan, a Washington, DC-based investor relations director who also runs the blog Off the Cuff. To spin an Old Yarn of your own, use the contact button above.

I grew up outside of New Haven in a pretty traditional preppy environment. But how you grow up isn’t always a good predictor of who you will actually become. While I muddled through public high school, my childhood best friend went to The Hopkins School, an exclusive day school founded in 1660.

This was part of his dad’s plan to develop the young boy into a Preppy with a capital P. See, my friend was never interested in the country club life or any of the other tweedy pursuits associated with being an Ivy Leaguer. Still, when he went off to college his dad sent along something like 20 pair of J. Press boxers.

I don’t think he ever took them out of the bag.

Once on his own, my friend promptly started a garage band and became an alt-rocker instead of a doctor or lawyer. His dad worked hard to become an establishment kind of guy, but try as he might to mold his son, my friend just wasn’t interested in that life. I always thought this was ironic as society puts so much emphasis on being born a blue blood, but just because you’re born to it doesn’t mean it’s who you want to be. — CHRIS HOGAN

Ivy-Style herein introduces a new series entitled “Old Yarn,” based on reminiscences and anecdotes about traditional American style. Spin an old yarn of your own by using the contact button above.

The blogger known as The Trad kicks off the series.

Back in Christmas of 1983, I spent my part of my winter break from college staying with a friend on the Jersey Shore. One day we went into New York, where I ran into another old friend who had transferred from my school to the screenwriting program at NYU. I also hit the winter sale at Brooks Brothers, where I bought a pink oxford-cloth button down.

Through a bizarre series of incidents, my new shirt wound up spending several months in the screenwriter’s apartment in the West Village, and finally in the office of the FBI, where the screenwriter gave it to a friend who worked in the bureau to bring back to me.

As the two talked the screenwriter began developing a story idea that later turned into the film “Thunderheart,” starring Sam Shepard as a corrupt FBI agent, and Val Kilmer as me.

That’s right: my buddy based the Kilmer character on me. Many college friends told me how they couldn’t stop laughing during the first 10 minutes, as the screenwriter had “nailed me.” I never saw the resemblance, but my friend assured me that Kilmer was playing me. And it never would have happened had it not been for my Brooks Brothers pink button down. — THE TRAD