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Cupid’s Capitalist: Meet Esther Howland, Creator Of The Modern Valentine

ove was very much in the air in February 1849. It had, in fact, descended on America like a thick, rolling storm front. In Philadelphia, S.G. Sherman advertised in the Public Ledger “the most beautiful assortment of valentines ever offered in this or any other city” at his Sixth Street shop. Further north, in Buffalo, Barnum’s Great Variety Store offered free “express carriage” delivery of valentines, ones sold at “lower prices than at any other establishment.” And the atmosphere was no different in New Orleans, where Thomas L. White ran ads for two and a half straight weeks, imploring customers to visit his store soon since “the day is near at hand.”

That day, of course, was February 14, St. Valentine’s Day, and Americans had been increasingly sweet on the holiday for the past ten years. Europe had embraced it several decades earlier, and the day’s origins stretch back further still. Chaucer described birds gathering to mate on “seynt valentine’s day” in his 14th-century poem Parliament of Fowls. Yet there was likely little in any of those stores in 1849 that was special or well-made. Valentines then were usually a cheaply made token of love, a few lines of rhyme on a slip of paper, often selected and printed by the shopkeepers themselves. (A typical verse: “My dearest dear and blest devine, I have pictured here your harte and mine.”) But starting that year, a 20-year-old graduate of Mount Holyoke College living in Worcester, Massachusetts, would begin to change that, helping usher in what is now a $20 billion holiday, a day when 145 million cards trade hands. That young woman was Esther Howland, who, 52 years later, would be judged by a Boston Globe reporter as not only the “pioneer maker of valentines” but also as a “monopolist.”

The Howlands had lived in Massachusetts since the Mayflower, ancestor John Howland making that fateful 66-day Atlantic Ocean crossing in 1620. Esther’s father, Southworth, owned a large bookstore and stationery shop in Worcester, which was well regarded for its collection of hymn books and Sunday School texts. But the Howlands also stocked valentines, including a more richly designed and lace-covered selection from England.

Those cards gave Esther an idea. Why not make similar-looking ones that aped the style of the British products? She would, in modern business parlance, go upmarket, selling cards for as much as 75 cents, an outrageous luxury at a time when the average American worker made less than a dollar a day (comparing costs before the Federal Reserve’s start in 1913 is tricky, but by comparison, the average worker currently makes around $125 a day; a similarly priced valentine today would work out to $100). In 1849, she created a few prototypes and cajoled her brother to hawk them in New York and Boston for her. In short order, she had orders worth a few thousand dollars. This prompted Esther to hire four women to help her, setting up headquarters in her family’s Worcester home and ordering a large supply of embossed English paper. The company that Esther would later formally incorporate as the New England Valentine Co. was born, and in the following year, orders doubled.  

Esther clearly understood something the shopkeepers creating inexpensive valentines either didn’t or figured wasn’t worth their time: branding. Each Howland valentine was stamped with a red capital letter “H,” and worked from the same palette: pastel oranges, greens and blues, full-color cupids and elaborate fronts to the cards made of lace, silk and satin. By 1864, the New England Valentine Co. had an agent selling its goods in Cincinnati, Ohio. Six years later, an outpost in Gold Hill, Nevada, was doing the same. There are various estimates of how well Esther was doing at the New England Valentine Co.’s height. In a late-in-life interview with Esther, the Boston Globe put her annual sales at between $50,000 and $75,000 a year, a massive sum at the time.

According to the Globe’s 1901 story, Esther had “monopolized the business in the United States.” In retrospect, the Globe seems to have taken some authorial liberties with the truth. Esther did indeed have some competitors, including one in New York that was about half her size. And she directly inspired some copycats, including her former apprentice George C. Whitney, who started his own valentine manufacturing company. And it was Whitney who would buy out Esther in 1881—the price he paid for the New England Valentine Co. was never disclosed—after a fall on an icy Boston street had left Esther confined to a wheelchair for several years.

The few stories that have been told about Esther over the years like to end on a note of bitter irony. They go a little like this: That Esther may have successfully commercialized love but apparently never found love herself, dying in 1904 unmarried at her brother’s Quincy, Massachusetts, home. Newspapers across the country reported on her passing, labeling her, variously, as “the inventor of valentines” and as a “New England spinster.”  

With the hindsight of a century-plus, there is perhaps a kinder way to conclude Esther’s tale. For like the greatest kind of love, her legacy has endured. So-called Howland Valentines are today a sought-after collector’s item. A 1997 Christie’s auction sold six for between $94 to $489. And some of her work resides alongside some of the greatest artwork in the world at the Metropolitan Museum in New York. The Met has several dozen Howlands in its collection, including one from near the end of Esther’s career, a 4-by-2-inch lacy ornament featuring pansies, roses and a collection of fruits around a banner reading “Affections Offering.” The card’s provenance is hazy, but the couple linked to it seemed content to let Esther’s work speak for itself. Its interior is signed, simply, “Gracie to Fred, 1880.”

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