Reggie Darling On Yale In The ’70s

At the recent “Ivy Style” symposium at the MFIT I had the chance to meet “Reggie Darling,” the man behind one of the more charming blogs written by a fiftysomething nostalgic for his vanished youth.

I’d told Reggie that I’d admired his reflections on the exhibit and thought many of his memories worth presenting to readers. He said he’d be honored, so here are his reminiscences on being a  social and sartorial traditionalist adrift in the post-heyday ’70s. — CC

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While I certainly enjoyed attending the “Ivy Style” exhibit, I had the eerie feeling while doing so that I was spending my time there staring at my own navel. It was all very familiar to me, and much of the clothing on display could have come from the closets and cupboards of the men in my own family. My roots in the Ivy League go back a number of generations, mostly at Yale, where my grandfather, father, brother and I were all fortunate to attend as undergraduates.

It was at Yale that I came to fully understand the true allure and iconographic significance of the Ivy style of dressing. While my prep school experience at St. Grottlesex prepared me for Yale in many ways, it was only upon my arrival in New Haven that I came to truly appreciate the splendor of traditional Ivy League dressing.  I came to Yale as a boy, and I left it as a man.

When my father was an undergraduate at Yale in the early 1940s, he was clothing obsessed. Letters written at the time to his parents in Grosse Pointe (which my grandparents saved and which I read many years later) were full of entreaties from him for yet more funds to purchase the clothing and sartorial accessories he felt were imperative in order to fit in with the smart crowd with which he ran at Yale.

Here’s his class photo from 1944:

For my father’s Yale 25th reunion, held in June 1969, I remember that all of his returning classmates were given blue-and-white striped blazers. However, the blazers handed out were made of paper, like the Andy Warhol soup can paper dresses that were a craze at the time. What I would give to have one of those blue-and-white striped paper blazers today!

One of my most treasured possessions is my Grandfather Darling’s blazer from the English public school he briefly attended before Yale. As the “Ivy Style” exhibit notes, much of the clothing adopted by American Ivy League undergraduates in the early twentieth century had its inspiration in England. But it became softer, less military, and less buttoned-up when it made its way to this side of the pond.

When I enrolled at Yale in the mid-1970s the Ivy League Look was in its death throes. Even though New Haven still had a number of Ivy style purveyors ringing the campus, almost all of them closed when I was an undergraduate there, with the exception of  J. Press (still going strong) and Barrie Ltd. (long-since closed).

My father used to let me charge clothes on his account at J. Press from time to time when I was an undergraduate. Nothing crazy, mind you. A sport jacket here, a couple of shirts there, some gray flannels, and a Shaggy Dog sweater or two. Just enough to keep me out of rags, I suppose.

My roommate and best friend at Yale, William Octavius Koenig IV (known as Willie), and I were among the handful of fellows in our class who appreciated the old Ivy League Look from the 1950s and 1960s, and we spent a lot of our free time (and most of our disposable income) at J. Press making pests of ourselves. One of the salesmen there, a fellow named Gabe, used to take us in the back room of the store and let us buy end-of-stock vintage shirts and ties from days gone by. Gabe used to sell clothes to my father, too, whenever he came to town. Willie and our friends used to call J. Press “the Squeeze” in those days, a play on its name and a comment on the injury that frequenting it did to our meager undergraduate bank accounts.

I was something of a throwback when I was an undergraduate at Yale. Although I was happy that it had gone co-ed by the time I arrived there, and many of my classmates came from backgrounds different from mine—ones that didn’t include prep school educations and legacy Yale histories—there was part of me that wished I had been born at a time when I would have attended Yale when it was still all male and more homogeneous and full of people like me, when people still dressed like the undergraduates shown in the following photograph from the 1950s that appears in the catalog from the “Ivy Style” exhibit:

But I didn’t, and it wasn’t, and they didn’t, and that’s more than okay with me.

There were still vestiges of that old Yale when I went there, though. Although official dress codes had been abandoned by the university during the previous decade, undergraduate men during my time at Yale in the 1970s were still expected to wear jackets and ties to university-sponsored events, such as receptions at the president’s house or athletic dinners. And, as a member of one of Yale’s undergraduate singing groups (and a highly social person to boot), I routinely found myself donning a jacket and tie at least several nights during the week. I also owned a tuxedo and a set of tails when I was an undergraduate there, and I had occasion to wear them, too.

During my senior year at Yale, when I was a member of the Whiffenpoofs, we spent a week or so traveling with the Yale Glee Club on a Midwestern tour over the Christmas holiday break, visiting places like Pittsburgh, Buffalo and Detroit. At the end of the tour, during the wrap-up dinner, I was given a gag award for being the “Preppiest Guy” on the tour, much to Willie Koenig’s irritation (he felt he was gypped out of that recognition). I wish I still had the certificate—that and a lot of other things from those happy, golden, bygone days.

After I graduated from Yale and moved to New York to begin my Wall Street career, I pretty much stopped going to J. Press, even though it had an outpost in the city. I missed Gabe from my undergraduate days, and the more urban, corporate Brooks Brothers seemed to me to be the more appropriate place to outfit myself as a junior banker than my old haunt of tweedy J. Press.

It was not until I was in my forties that I found my way back to the Squeeze again. I’ll never forget the time I walked into the old store on 44th Street, the one around the corner from Brooks, and how I almost started to vibrate when I tried on the same suits and jackets there that I remembered my father wearing. Here I was, all grown up, slipping my arms into the very same tweed jackets and worsted suits that my father wore when he was the same age as I had become.

Not surprisingly, I still mostly outfit myself from the likes of J. Press and Brooks Brothers. I also shop at specialty stores that sell traditional men’s clothing and accessories inspired by the Ivy League style, in some cases updated for a more modern sensibility. I like the look, I feel comfortable in it, and it is one that is appropriate for men of all ages to wear. — REGGIE DARLING

15 Comments on "Reggie Darling On Yale In The ’70s"

  1. Nice reflections indeed Reggie. Thank you for sharing.

  2. I really enjoyed this piece after Mr. Press pointed it out in your comment section and just enjoyed reading it again. Reggie’s newest post on his blog about Alden loafers and why he wears them is pretty great as well.

  3. Fantastic!!!

    I am so jealous that I wasn’t born into this. I will only ever know of this world from a distance.

  4. Note to readers who missed our earlier post about tech difficulties. They’ve been ironed out, but at least three posts were sucked into the ether when our hosting surface migrated us to a new platform. Those posts will be rebuilt soon.

  5. Thank you, Christian, for hosting me here on your terrific blog. It is an honor, indeed! With many thanks and much appreciation — Reggie

  6. Be still my heart!

  7. Reggie, I read your post on Alden slip-ons and, having grown up on DC, was reminded of the Georgetown University Shop…not entirely sure why that popped into my head. But a wonderful post.

    While I’m indifferent to the term, the word “gyp” is commonly thought to have its origins in the word gypsy and is considered by many to be a slur.

  8. What a great post. It definitely stirred some deep set emotions about family history and the passage of time for me. A little teary eyed, a little nostalgic, a little hopeful. Thanks!

    ” I wish I still had the certificate—that and a lot of other things from those happy, golden, bygone days.”

  9. St. Grottlesex? Wow.

    Even if you hired a comedy writer tried to come up with a name for a prep school, there’d be no topping that.

  10. The collar poking above the Yale sweater – is that Ancient Gordon Dress tartan?

  11. Grottlesex refers to a collection if schools. It does sound pretty dirty, doesn’t it?

  12. Thanks for sharing. My grandfather, a J Squeeze man, is also in the Branford ’44 class photo.

  13. Nice post. My father was Yale ’49. I remember as a kid wearing a Gant shirt from the Yale Coop that had been given from my father to my mother and then passed on to me.

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