The year is 2010. My 8 year old self is sitting in computer class, seeing how many funny clip art images I can insert into my newly opened word document before the teacher notices that I’m wreaking havoc on the crisp new page that he just had us open. Being only 8 years old, the assignment he’s explaining to us is not a soul-crushing 10 page essay due in a week that will make me question my decision to go to college, but rather a Microsoft Word exercise where all I have to do is learn how to add a border and some word art. Ah, what a time. I’ve just finished adding a low-resolution christmas tree border to my document (and being exuberantly proud of my choice), when the teacher instructs us on how to change the font on our page. Choose any font that you like, he says.
My small fingers scroll maddeningly through the hundreds of font choices. I pause briefly on the classics: Comic Sans, Papyrus, Jokerman, Broadway. Endless possibilities. At last, however, my cursor pauses on something new, something unexpected: Wingdings. A font full of images? What could it mean? I knew it had to be the one, giggling as I typed nefarious words in the hidden typography.
I remained curious about the font for many years to come. All throughout elementary school I would pause on the cryptic preview when looking for a font, wondering about its purpose. I had always assumed that it was nothing more than a gag, intended to be wacky and confusing for those who stumbled upon it. It wasn’t until I was older that I suddenly remembered this curious moment in my childhood, and realized that there probably was a logical purpose behind the font that my 8 year old brain found so amusing.
If you aren’t familiar with Wingdings, it’s a font choice originally released on Microsoft Word that is made up entirely of symbols and simple images, each corresponding to a certain keyboard key. There are so many different symbols that the font is a family of multiple versions, including Wingdings, Wingdings 2, Wingdings 3, and the recently added Webdings.
The font style appears almost like an early-internet version of emojis. After some research though, I discovered that the purpose of Wingdings was actually quite utilitarian in comparison to peach or heart eye emojis. People today send images regularly, whether that be through text or email, or word processing documents. In the world of high-speed technology, sending photos is effortless. However, in the early 2000s, at a time when technology like Microsoft Word and email were just starting to develop into what they are today, sending image files was much trickier. Computers and other data storage devices often couldn’t handle the large file sizes that came with images. Even if they could, image files often had to be imported at very small sizes or resolutions (hence the grainy quality of many 2000s era websites).
Enter Wingdings. Image fonts like Wingdings, also referred to as Dingbat fonts, provided a way for people to access simple high-quality images that were easy to use alongside other font characters (because the images acted as a font themselves). Someone could simply “insert” the image using the correct letter key, and then scale the image larger or smaller by adjusting the font size.
Wingdings was originally based on a font created by Charles Bigelow and Kris Holmes under a different name, which was then purchased by Microsoft. As for the odd name choice: Wingdings is supposed to be a mashup of the word “Windows” (Microsoft’s operating system) and “Dingbat”. This can be traced all the way back to the printing press era when ornamental designs, aka “Dingbats” could be added into a typeset to add decorative elements to books and flyers.
Despite this ultimately simple explanation for the font’s existence, it has long been met with suspicion. Throughout the years, many have tried to read too deeply into Wingdings’ cryptic messaging, finding hidden meanings in the arrangement of the different symbols. The font even came under scrutiny when someone pointed out that the symbols for NYC came out to a skull, the star of david, and a thumbs up, which was said to have been an act of antisemitism against jews in New York (This was claimed to be a coincidence by Microsoft, and the symbol arrangement was notably altered when the new version of the font, Webdings, was released years later).
After living most of my life being curious about the purpose behind Wingdings, the ultimate explanation came off as, well, pretty practical. I no longer felt the same sense of mystery or humor surrounding the font. If anything, the more I thought about it the more it became clear that Wingdings is simply a good example of technology that has been rendered obsolete (despite being in its prime only a decade or two ago). Much like certain tools and technologies from thousands of years ago, which we can only guess at the purpose behind, Wingdings has begun to fade into history. So much so that its fairly obvious purpose has been written off as a mystery or a gag.
The more I thought about Wingdings the more I pictured some 8 year old of the future, giggling over our modern day technology that I use every day, or rendering it absurd. What was a computer used for anyway? I don’t know if I like to think about it.
