The student there who seemed to me most preppy—by virtue of his clothes and demeanor and attitude—was a very attractive young African American lad of seventeen. We had some chitchat afterwards. I said, “Let’s stay in touch.” We exchanged e-mail addresses, whereupon I learned that his name was Jordan Buxton-Punch. John Knowles and Louis Auchincloss would be hard-pressed to come up with a better name.
I saw him just the other day, about a year later, when I gave a talk at Yale. He’s a freshman now. I wonder if Jordan considers himself a “preppy”? Post-preppy? I wonder if, when he reaches fifty-seven, he’ll still think of himself as a product of our once-rarefied world?
Portsmouth Abbey, Yale
Take the Steamship Authority ferry from Woods Hole or Falmouth to Martha’s Vineyard and—voilà!—you are in the heart of the black prep experience. Of course, Sag Harbor—on the extreme east end of Long Island—has long been home to the same crowd, too, but islands, which require boats, are inherently preppier. Families and singles, many wearing the preppiest of foul-weather gear, head over to their country houses to spend as much of their summer as they can on the island.
That guy in the Wharton ’82 baseball cap? The managing partner of Morgan Stanley. The woman in the Lilly Pulitzer pants and polo shirt? The top producer at Corcoran real-estate brokerage. What about that guy in the seersucker blazer talking quietly on the phone? Oh, he’s an undersecretary of state. The kid in the webbed belt and Andover T-shirt? He goes to Andover, silly.
Look at yourself: What are you wearing? An old pair of khaki shorts with that faded ketchup stain on them? Your big brother’s frayed button-down shirt? Pull yourself together and go for lunch at Farm Neck Country Golf Club. (As is the Vineyard’s wont, it is totally inclusive, open to the public, and nicely maintained.) Take a left at Cornel West and plop yourself near Vernon Jordan.
The majority of tony black resorts trail down the East Coast, from Massachusetts to Florida. Oak Bluffs and Sag Harbor are by far the best-known communities, and draw elite African Americans from all over the country, though neighboring towns have been integrating since the mid-1960s.
Other vacation communities include:
IDLEWILD, MICHIGAN. Known as “Black Eden,” it was started by black professionals in 1912 as a haven for families living in Detroit, Chicago, and throughout the Midwest. With 1,300 acres around a lake, it earned its name allegedly because its “men were idle, and its women were wild.”
HIGHLAND BEACH, MARYLAND. Founded in 1893 by Charles Douglass, son of the abolitionist Frederick Douglass. He and his wife bought forty acres on the Chesapeake Bay for a summer resort for their family and friends. W. E. B. DuBois, Paul Robeson, and Harriet Tubman lived or visited there. Today it is a year-round community, though it’s especially lively as a summer destination for Washingtonians and Baltimoreans, many of whom are descendants of the original settlers.
ARUNDEL ON THE BAY, MARYLAND. Approximately five miles south of Annapolis, Maryland, Arundel on the Bay was started by well-to-do black families who had few summer options. Today its 345 houses have a diverse population. Arundel on the Bay has a private beach, pier, and boat launch, as well as its own fan page on Facebook.
Deborah Solomon:
“[The name] Skip sounds so WASPy.”
Henry Louis “Skip” Gates Jr.:
“Hey, you know, I don’t think we knew what
a WASP was. I didn’t realize it until I went
to Yale as a student and met ‘Chip’ and
‘Muffy’ and—actually, I thought ‘Skip’
was a black name.”
Where do preppy gays go? They go everywhere and anywhere because they feel entitled, but even in the usual places (Provincetown [1.], say, or Fire Island Pines) they like to arrive after the season is over (late September) or in a vintage yacht or a spectacular sea plane, and they’d rather stay off the beaten path—in Water Island (2.) rather than the Pines, for instance.
Palm Beach (3.) is a current attraction for gay preppies. South of Sloans curve, the old “Bar Mitzvah Buildings” on the beach are being bought up by gay prepsters; they love the mid-century yellow-and-white wallpapers and the blue kitchens with blue appliances. On Thursday in Palm Beach there’s gay night (“Gentlemen’s Night”) at the Colony Hotel’s Polo bar. Now there are even (sort of) out gay preppies in the infamously exclusive Bath and Tennis Club (B&T).
Middleburg, Virginia (4.) is the mecca of the gay horsey crowd. Preppy gays love riding, teaching dressage, even hunting (if they can afford it).
Washington D.C. (5.) is gay preppy central—all those well-paying government jobs immune to economic downturns, all those gay preppy colleges (especially Georgetown), and then there’s the Hill with all those power-hungry homos who start early as snarky pages.
Yale (6.) is definitely the gayest of the Ivy League universities.
Moving up the map, there’s Southampton (7.), so much preppier than Easthampton or Sag Harbor. Go to Flying Point Beach and watch Prince Dmitri of Yugoslavia rubbing suntan oil on his boyfriend’s muscled back. If you can, buy a big house and join the Meadow Club. If all you can afford is a pink-and-green outfit, then become a walker for an attractive widow and get her to take you to the Beach Club, where you might find someone to date for the rest of the summer.
All along the Hudson Valley (8.) there are what might be called the “Merchant-Ivory” breed of gay preppies in their Greek Revival country manors and dolled-up Victorian mansions—“preppies” by self-appointment, though they probably don’t know what states Andover and Exeter are be located in. Litchfield County has all those gay couples dying to do a benefit with Anne Bass or Diane von Furstenberg, not because they really care about their charities but because they do want to know those ladies.
Greenwich, Connecticut (9.); all of Vermont (10.) except Burlington; Newport, Rhode Island (11.); Maine (12.) around Blue Hill and Bar Harbor—those are all the Elysian Fields for the good, the gay, and the prepped-out.
In the Midwest there’s Mackinac Island in Michigan (13.) (where cars are forbidden and everyone rides around in horsedrawn carriages past huge white summer houses) as well as Grosse Pointe and Bloomfield Hills, home of the automobility. In Chicago (14.) there’s the North Shore, especially Lake Forest (pronounced “Farest”). In Cincinnati (15.) there’s Indian Hill and in Cleveland (16.) there’s Shaker Heights.
On the West Coast there’s Sonoma County (17.), of course, which is close to San Francisco (18.), but the epicenter is Montecito (19.), where rich gays mix freely with rich straights (fund-raisers for the Santa Barbara Art Museum are at the very cross-section of the two worlds, where they show up in nearly equal proportions).
Of course anywhere in Kansas (20.) where there’s a Princeton alumni event, or in New Mexico (21.) where the opera crowd mixes with the painters, you can find gay preppies. Remember, no matter where you are, look for the horsey set or join the subscribers to the symphony and you’ll find gay preppies within five minutes.
Horses and classical music—those are the two big magnets for the gay elite.
For some men, the term Preppy is practically synonymous with Sissy. Ronald Reagan on George H. W. Bush: “A Yalie, a preppy, a sissy.” As with preps, naturally there are areas of gay concentration where they can comfortably huddle with sympathetic peers. When the two groups intersect you have, well, David Hyde Pierce. Here’s a look at the gay prep landscape, where at any time one can feel free to wear his pastel-colored cashmere sweater tied around his neck as a scarf. With pride.
Think about it: androgynous haircuts, sensible shoes, plaid, a love of golf matched only by a disdain for sex in general. What could be preppier? From Nancy Kulp (representing Northampton, Massachusetts, 22.) to Jodie Foster to that woman who left her husband for Martina Navratilova, prep lesbians (dare we say “presbians”?) have been with us long before Gertrude Stein ever started writing those strange little poems. Whether they’re grooming the horses, fixing the station wagon, organizing some sort of an
gry protest, or just helping you improve your tennis swing, it’s more than likely there’s a presbian in your life. Hey, someone has to run things.
As you pass through the grosgrain pillars of our Pantheon, we expect you will be inspired by the legacy of those who came before you. They may have achieved prominence in the arts or in industry. They may be philanthropists or authors. Wastrels or world beaters. They may have left the world a better place than when they first found it. They may have left the world a worse place but scattered fun nicknames around. (“Brownie, you’re doing a heck of a job.”) Some of them are historic figures; others have yet to enter their primes. And yet they’ve all earned entrance into this exclusive club through some form of preppiness. They didn’t all start out that way, but they have added dash and spirit to their personal and thus our collective histories. And, oh, yes. Many of them are interconnected.
Jonathan Adler (b. August 11, 1966) From his bio: “1979: Begs parents to buy him a wheel and a kiln … 1980–1984 spends entire adolescence in basement … throwing pots. 1984–88 Allegedly studies semiotics and art history at Brown but actually spends all his time at RISD throwing pots. 1989 … Evil professor advises him to bag pottery and try a career in law … 2003 … Develops raging obsession with waspy country-club style … Concerned Jewish mother schedules an … intervention.”
Josephine Patterson Albright (December 2, 1913–January 15, 1996) Although she was born into the powerful Medill journalism family in Illinois (Northwestern’s journalism school is called Medill), Josephine and her older sister, Alicia, were raised as socialites. Her father, Joseph Medill Patterson, founded the New York Daily News and cofounded the Chicago Tribune. His sister, Eleanor Medill Patterson, was the publisher of The Washington Times-Herald. Mr. Patterson forbade his daughters to go into the family business but approved of Josephine getting her pilot’s license. At sixteen, Josephine did just that, and she was the youngest pilot to fly the mail route between Chicago and Saint Louis. Josephine attended the Foxcroft School in Virginia, and during her debut at eighteen, she and her sister decided to fly to India to shoot tigers. They left Chicago without telling their mother. When Josephine killed her first tiger, Alicia became annoyed and told Josephine not to come on the next hunt. As her obituary in The New York Times described it, “So Josephine went on the next hunt carrying only a book. She was sitting in a tree reading when a leopard bounded up behind her. Josephine threw the book and hit the leopard in the nose. Alicia finished it off.” After this whirlwind adventure, Josephine defied her father and began writing for his rival newspaper, The Chicago Daily News, where she did hard-core crime reporting (think Roz Russell in His Girl Friday). She met lawyer Jay Frederick Reeve then, and once married, she opened a pig and dairy farm that became a major success. After divorcing Reeve, Patterson began raising stallions in Wyoming. She married painter Ivan Albright in 1946 in Montana. Together they traveled widely and had four children. From 1949 to 1952 Mrs. Albright wrote a column for Newsday (the Long Island, New York, newspaper founded and run by her sister, Alicia). After Alicia’s death, Josephine established the Alicia Patterson Foundation, which awards fellowships of six months to a year to journalists.
Tina Barney (b. October 27, 1945) Photographer of the inner sanctums of prepdom. A graduate of The Spence School, she began taking arresting, outsize color photographs of America’s blue bloods (her family and friends) that caught their rituals in such places as Locust Valley, Rhode Island, or Sun Valley. Family function and dysfunction close-up. She also photographs the blue bloods of Europe. Her work is collected in many museums, including MoMA in New York and the Museum of Fine Arts in Boston.
Leonard Bernstein (August 25, 1918–October 14, 1990) This Massachusetts native, who at fifteen changed his name from Louis to Leonard, studied the piano, despite his father’s discouragement. After Boston Latin School he studied music at Harvard. In 1943 Bernstein, then the assistant conductor of the New York Philharmonic, became an overnight star when he took over at the last minute for conductor Bruno Walter, who had fallen ill. Besides conducting, composing classical music, hosting the “Young Peoples’ Concerts” from 1958 to 1972 (the longest-running program ever devoted to classical music on television), and composing the scores of West Side Story, On the Town, and Candide, Bernstein was also famous for hosting a cocktail party in 1970 for the Black Panthers, which was in many ways the first instance of political correctness. Tom Wolfe (see Tom Wolfe) wrote about it in Radical Chic & Mau-Mauing the Flak Catchers. Bernstein left his wife, Felicia, in 1976 in order to live with a male lover, though he returned to take care of her when she was ill. Bernstein was a Jew, a genius, a bisexual, a provocateur, and a preppy.
Stephen Birmingham (b. May 28, 1932) This Hartford native and Williams College graduate started his career writing advertising copy for a New York department store before plunging into commercial nonfiction. A lifelong interest in the privileged classes resulted in more than thirty books, road maps to America’s various elites: Our Crowd, Real Lace, Certain People: America’s Black Elite, The Grandes Dames, California Rich, and The Wrong Kind of Money among them.
Cory Anthony Booker (b. April 27, 1969) The mayor of Newark, New Jersey, since 2006 is the son of a couple of early African American IBM executives. Booker played football (he made all-American) for a largely white high school in New Jersey and, at Stanford University, continued to play varsity football, this time making the All-Pacific Ten Academic Team. He spent five years in Palo Alto, getting his master’s in sociology, went to Oxford on a Rhodes Scholarship, and then to Yale, where he earned his law degree in 1997. In his first term he lowered crime and created more affordable housing, and has been the focus of an unusual amount of attention: He was the subject of a multipart documentary on the Sundance Channel, and got into a faux feud with Conan O’Brien (see Conan O’Brien).
Sandra Keith Boynton (b. April 3, 1953) When she was two, Sandra’s parents became Quakers, and Boynton spent her youth at Germantown Friends, a Quaker school in suburban Philadelphia. Her father taught English and was the head of the upper school there. At Yale, where she was in the second coed class, Boynton ended up marrying a fellow Eli, and they had four distinguished offspring together. Meanwhile, there were the greeting cards. Preppies may not know a Monet from a Manet, but they certainly know their Recycled Paper Greetings by Boynton. This artist is responsible for the cards with whimsical animals that have jollied away our fear of growing old. She has sold well over 200 million of them.
Benjamin Crowninshield Bradlee (b. August 26, 1921) If for no other reason than he owns Grey Gardens … really, we love the crusading former editor of The Washington Post Ben Bradlee. Another descendant of early Americans, Bradlee is a born patrician whose family tree included the creator of Vanity Fair magazine, an ambassador to England, and an all-American football player. He graduated from St. Mark’s School, and at Harvard played football all four years, was tapped for the final club AD, and majored in classical Greek—a major that is prep because it is as far as one can get away from being practical. During World War Two, Bradlee served on a naval destroyer in the Pacific. In 1946 he began his career at a New Hampshire newspaper, moving to The Washington Post in 1948. He went to Paris in 1951 to work in the press office of the American embassy, and then at the USIE (forerunner of the USIA), disseminating American propaganda and working with the Voice of America. Bradlee joined Newsweek in 1953, first in Paris and then in Washington, where his crowd included Senator and Mrs. John F. Kennedy. As Washington bureau chief of Newsweek, he helped steer the sale of the magazine to his friends the Grahams, who owned the Post. In 1968, Bradlee was named executive editor of the Post, and he took on the Nixon White House, allowing the ad hoc investigative team of Bob Woodward and Carl Bernstein to dig deep into the Watergate scandal. Bradlee was portrayed by Yankee actor Jason Robards Jr.—perfect casting—in the movie, All the President’s Men.
Kingman Brewster Jr. (June 17, 1919– November 8, 1988) This direct descendant of Mayflower t
icket holder William Brewster, a Plymouth Colony pilgrim, was raised in New England. After graduating from the Belmont Hill School, he went to Yale. Brewster achieved campus-wide fame—or notoriety—by turning down Skull and Bones. Chairman of the Yale Daily News, as a student he had been opposed to America entering World War Two, but he changed his mind after the bombing of Pearl Harbor, when he enlisted as a naval pilot. He entered Harvard Law School after the war, and was an editor of the Law Review. Brewster went to Europe to work on the Marshall Plan, and returned to join academia, first as a professor at MIT, and then at Harvard Law School. He is best known, however, as president of Yale, from 1963 to 1977, the years of long hair, Vietnam protest, and the sexual revolution. During and thanks to Brewster’s tenure, Yale went coed, demoted ROTC from an academic program, hired the Rev. William Sloane Coffin (Yale alum, Skull and Bonesman, and CIA operative) as its chaplain, and supported him as he became an ardent anti-war activist. From 1977 to 1981, Brewster served his country as President Carter’s ambassador to the Court of St. James.
Thomas John Brokaw (b. February 6, 1940) While Brokaw has professed to be an “anti-preppy,” the longtime anchor and managing editor of the Nightly News on NBC (1982– 2004) is included here for his boyishness as a newsman, making him prep whether he likes it or not. The eldest of three sons born in Webster, South Dakota, Brokaw attended public schools and went to the University of Iowa. He dropped out, claiming he “majored in beer and coeds” (so prep it hurts), then went to the University of South Dakota, from which he graduated. He also received honorary degrees from such prep institutions as the College of William & Mary, Dartmouth, Duke, and the University of Pennsylvania. Brokaw and his wife sent their three daughters to private schools. He is a confirmed outdoorsman, and consequently has aged perfectly.
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