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Why the Wingdings font exists

Wingdings is the font made entirely out of symbols. But why?

It seems as bizarre as it is ubiquitous. What is Wingdings thinking? Why would someone want to write a comma using a mailbox? Why would anyone think we want to compose in peace signs and crosses and heart shapes? The below is just a brief example of Wingdings weirdness:

Wingdings and friends

Wingdings and friends. (Vox)

But Wingdings is much more than just a quirky font. It was —and remains — a phenomenon. In the early '90s, it was one of the first times people realized fonts could break through to the mainstream. One of the creators of Wingdings, Charles Bigelow, of the legendary design studio Bigelow & Holmes, told me Wingdings marked one of the first times a font became part of the popular culture.

And when you delve into how Wingdings was born, it becomes clear why it become so iconic.

Who made Wingdings — and why

Wingdings came from somewhere

Wingdings came from somewhere.

Vox

As a means of writing sentences, Wingdings fails — but that was never its purpose. It was created to be used as a unique tool for the pre-internet era. It was akin to emojis, but with even more utility.

Today it's easy to cut and paste images from the internet, but it used to be a lot harder. There were few ways to get images, files were way too large for puny hard drives, and they were of poor quality. Even worse, it was tough to get pictures to play nicely with text. Fonts like Wingdings provided a workaround by giving people high-quality, scalable images that didn't clog up their hard drives.

Two people made Wingdings happen: Charles Bigelow and Kris Holmes (proprietors of the firm and husband-and-wife team). As designers of the font Lucida, they crafted pioneering type uniquely suited to the digital era (you can read Bigelow & Holmes's thesis on Lucida's unique traits). They were protégés of legendary designer Hermann Zapf, whose own Zapf Dingbats font, another collection of odd symbols, broke ground when it was distributed with Apple Printers in the mid-1980s.

With Lucida, Bigelow and Holmes were at the vanguard of digital type designers. But to be complete, their font needed complementary characters that worked well with letters, so they designed them in 1990.

Originally three separate fonts called Lucida Icons, Lucida Arrows, and Lucida Stars, the fonts that became Wingdings were crafted to harmonize with text and made with similar proportions to Lucida. Users could then pluck the appropriate icon, by typing the letter assigned to it, to ornament, animate, or otherwise adorn their documents without worrying about file size or poor quality.

Microsoft includes Wingdings with Windows

Bill Gates in 1986

Bill Gates in 1986.

Joe McNally/Getty Images

The breakthrough happened soon after: Microsoft bought the rights to Lucida Icons, Lucida Arrows, and Lucida Stars in 1990, and combined its favorites into a single font called "Wingdings" that was included in a beta test of Windows that year. Storage size limited how many characters the company could include — it was only willing to include so many fonts in its floppy disc release. But despite the technological limitations, a cultural phenomenon was born.

Microsoft called it "Wingdings" to combine an old printing term, "dingbat," with "Windows" (more on dingbats later). The new name had "the added connotation of suggesting wildness and excitement," Bigelow says, "like 'a real wingding.'" From the beginning, Wingdings was a hit, thanks to its inclusion in the Microsoft ecosystem, which doubtless helped it become more well-known by average users than Zapf Dingbats and other competitors.

From the beginning, Wingdings amazed, amused, and (occasionally) confused people

Not everybody knows what to do with a Wingding.

Not everybody knows what to do with a Wingding.

Vox

As today, Wingdings was occasionally misunderstood. While it was intended to be picked apart, used individually for a splash of imagery, users interpreted it as an unusual font for writing words. That had unexpected consequences.

"It turned out that Wingdings caused more excitement than Microsoft expected," Bigelow says. "Conspiracy theories sprang up that Wingdings contained hidden messages." Most famously, Wingdings supposedly contained anti-Semitic messages against New York City (when users typed "NYC," the Wingdings for a skull, a star of David, and a thumbs-up appeared). Of course, Bigelow notes that the "hidden messages" were simply an accident of the font conversion process — Microsoft hadn't considered that users would read the grab bag of Wingdings images as a code for actual letters.

Those conspiracy theories, as flawed as they were, ironically showed what a success Wingdings had become. "It was entirely accidental," Bigelow says, but it was, "a vivid lesson in the emerging social psychology of mass-market computer use." Wingdings was impacting the culture at large. From there, it was further adapted through additional icons and images, mutated forms like Webdings (which Comic Sans designer Vincent Connare worked on), and other iterations.

Why certain symbols became Wingdings

"We were influenced by images from similar historical and modern sources," Bigelow says. The Lucida Icons spanned many eras. "Pointing fingers and hands go back to medieval manuscripts and, before that, to ancient Roman gestures; airplanes are 20th-century inventions; and keyboards, computers, computer mice, and printers, included in the Lucida Icons fonts, were part of office life in 1990 when we drew the images."

Charles Bigelow's favorite Wingdings are the floral elements, or fleurons, which were partly inspired by flowers in his and Holmes's garden the summer they designed the font. Others are inspired by Renaissance printing, English roses, and other foliage:

Charles Bigelow's favorite Wingdings

Charles Bigelow's favorite Wingdings.

Charles Bigelow

It makes sense that Wingdings drew from printing heritage — the font goes back not just to the digital era, but hundreds of years before that.

Wingdings got its name from printers' dingbats

An illustration of a 17th century printing press

An illustration of a 17th-century printing press.

Universal Images Group/Getty Images

We know that Microsoft named the font "Wingdings" by combining "Windows" and "dingbat." But what's a dingbat?

When using a printing press, printers needed a shortcut when it came to ornamenting their text. Every figure or letter had to be hand-carved and laid out before anything could be printed, so it was too laborious to make a new template for every drawing or figure.

Enter dingbats. These tiny pieces included a variety of reusable shapes that could be slotted into text and used as ornamentation in a book.

"They've been around as long as type has been around," says Nick Sherman, a typographer and typographic consultant. "It all started with ornamentation of title pages and things like that."

The same way a Wingdings user might slot in a Wingding mailbox while asking for an RSVP, an analog printer could use a dingbat to quickly add some flair to a page.

As for where the "dingbats" name came from, nobody knows for sure. "A lot of printing terms start as a colloquial thing," Sherman says. Bigelow notes another possible origin: "dingus," a Dutch word for thing. It could also be an onomatopoeic invention, like the sound of a piece of metal type falling on the floor.

Wingdings points to a picture-filled future

Wingdings point to the future

Wingdings point to the future.

Vox

The history of character fonts goes back even further than the dingbat. Bigelow, who taught Concepts of Text at Stanford, among other courses, sees a long through line from ancient text to the present. (After all, he notes, it's possible to trace even the letter "A" to a picture of an ox head 3,500 years ago). That ancient use of pictures has continued to the modern era.

"Emojis are like dingbats in being typographical symbols," Bigelow says. "But they also hark back to the ancient concept of picture writing from which pictographic-ideographic-logographic Chinese characters and kanji evolved." Chinese and Japanese writing came from pictures and, like today's emojis, are ways of expressing our ideas and ourselves.

The future of fonts like Wingdings, which occupy a weird space between pictures and text, is impossible to predict. Will emojis become the main means of communication? Will people ditch text altogether? If so, make sure you know your Wingdings well — you're going to need that mailbox.