It’s so distant now—even though it wasn’t all that long ago—that hardly anyone remembers anymore. But there was once a time when the most potent examples of the aspirational dream weren’t movie stars or social-media influencers but the myth-like creatures of fortune and family name whose sparkling existence was the stuff of American fairytale. Take the largely forgotten Sanford family of Amsterdam, New York, who amassed a near-Vanderbilt-size pile of dosh, thanks to the ingenuity of John Sanford, the family patriarch, who, as a manufacturer of carpet, beginning in the 1840s, planted the seeds of an improbably glamorous empire. Over the next several generations, the family grew their wealth and political influence; three Sanfords became US congressmen. Along the Eastern Seaboard, the name also gained the luster of upper-crust aplomb. No more so than in the 1920s when two new shoots of the tree, a brother and sister by the name of Stephen and Gertrude, emerged destined to achieve something more than just a normal old fabulous life.

RIDE OF A LIFETIME

Stephen “Laddie” Sanford (top), photographed by Slim Aarons, in 1955; saddled up in Santa Monica, circa 1930s.

“Laddie,” as Stephen was called, naturally attended St. Mark’s, Yale, and Cambridge, more for social and sporting reasons than pure academics. He was, in fact, the poster boy of the genteel athlete, as Slim Aarons’ unforgettable portrait of him at rest between chukkers one languid afternoon at the Gulfstream Polo Club, in Delray Beach, Florida, indelibly records; the number four on his jersey signified his position as a defenseman on the team he funded, the Hurricanes. He carried a 7-goal rating—an achievement in saddle and mallet skills that made him one of the best American polo players of the 20th century. He was also one of its “best mounted.” (In 1922, he bought a polo pony named Jupiter for $22,000, the most ever paid.)

His other expensive obsession was the steeplechase, which combined big money, serious danger, speed, and international appeal—the F1 of its time but on a horse.

Although he also maintained an active role in the New York–based family business, he rotated houses, as people of his type and bank account did back then, with the changing of the seasons. Summer: Palm Beach, where he played polo; fall: mostly on the road, following his racehorses as they competed at various venues; winter: New York, where, for a time, he lived at his father’s house, a 25,000-square-foot Beaux Arts masterpiece designed by the celebrated architects Carrère and Hastings. (The Gilded Age building is one of the last of its type still standing, and happens to sit catty-corner to the Rhinelander mansion on Madison Avenue and 72nd Street, which has been the Ralph Lauren flagship since 1986.)

His other expensive obsession was the steeplechase, which combined big money, serious danger, speed, and international appeal—the F1 of its time but on a horse.

It was there that Laddie’s youngest sister, Gertrude—an original prototype of the unconventional society heiress with antsy energy and nose-thumbing bohemian confreres—often bunked down, too. An adventurous personality who wore her hair bobbed, her itch was danger: lion safaris in Africa; joining the O.S.S. in World War II; getting captured by the Germans and then escaping a prison behind the lines. These exploits burnished rather than made her fame, which had begun at the age of 26, when her friend, the Broadway playwright Philip Barry, wrote Holiday, basing its heroine, Linda Seton, on Gertrude’s life of charmed defiance.

More recognition followed when the director George Cukor cast Katharine Hepburn in the role for his Hollywood adaptation. The movie, which also stars Cary Grant, is one of Cukor’s great screwball comedies. Holiday came out in 1933, the worst year of the Great Depression. The country needed a laugh, a boost, a vision of possibility and hope evoked by a carefree world of elegant taste and scenery. At their best, screwballs—It Happened One Night, Bringing Up Baby, His Girl Friday—didn’t just have clever twists in plot; they also had biting things to say about class snobbery and the battle between the sexes. As a woman who bucked social expectations and married a man who himself didn’t kowtow to the group boorishness of male behavior, Gertrude was a perfect model for such a character. She later wrote a colorful memoir, The Time of My Life, under her married name, Gertrude Legendre, that, like others of its type and time, is more an exercise in self-mythology than self-examination.

Laddie is also thought to have inspired a character in Holiday—that of the tipsy brother who can’t escape the confines of his father’s shadow—but the facts don’t quite square. In 1933, for instance, instead of a debutante, he married the Hollywood actress Mary Duncan. It was an early example of the now common old-money-meets-showgirl scenario that once filled newspaper columns and now fuels many a social-media scroll. Laddie also threw money around, but it usually paid off. The Hurricanes won the U.S. Open Polo Championships no less than five times between 1926 and 1949.

His other expensive obsession was the steeplechase, which combined big money, serious danger, speed, and international appeal—the F1 of its time but on a horse. The Grand National, held in Aintree, England, was, according to one magazine, “The most hazardous 4 miles known to the racing turf.” It was also the most prestigious. In 1923, with both king and queen among some 100,000 onlookers, 28 horses started the race. Only seven would finish, and for the first time in history an American-owned horse would win. His name was Sergeant Murphy, and the owner was Laddie Sanford. To understand the magnitude such news once carried, Time magazine put Laddie on its cover that March between issues that featured the Nobel Prize–winning writer Joseph Conrad and Mustapha Kemal Pasha, the founder of modern-day Turkey. In the end, though, it wasn’t the timeless classic movie or the grand trophy that situated Laddie on the ultimate mood board of memory. It was Aarons’ photograph, and its captive details: the dog skippering through the frame; the purple-and-gold pageantry nodding to the sport’s royal lineage; an armful of banged-up mallets tossed into the back of a trusty old station wagon. At some point, the image also caught the eye of a young tie designer from the Bronx, who had settled on naming his fledgling company after a particular international equestrian sport. In it, he spied something authentic and uncontrived, effortless and true. Which reinforced his idea that clothes aren’t just clothes but the accelerant of dreams.

---