You’ve definitely seen them. You might have even accidentally typed a row of them while desperately trying to fix a printer error or clicking the wrong thing in a Microsoft Word dropdown menu. A mailbox. A tiny little bomb. A hand pointing right. A "Victorian" looking cross. This is the weird, slightly chaotic world of Wingdings. It isn't just a glitch in your computer, and it definitely isn't a secret code for the Illuminati, despite what some 1990s conspiracy theorists might have told you.
Essentially, Wingdings is what we call a dingbat font.
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Wait, what's a dingbat? It sounds like an insult your grandfather might hurl at someone in traffic, but in the world of traditional typesetting, it’s a real term. Before digital screens existed, printers used small ornamental characters—flowers, boxes, or stars—to fill up space or mark the end of a chapter. They were the ancestors of the modern emoji. When the digital age rolled around, Microsoft needed a way to give users high-quality graphics without hogging all the memory on a 1990-era hard drive.
The Weird History of How Wingdings Happened
Back in the early 90s, the internet wasn't the image-heavy playground it is now. Loading a single JPEG could take long enough for you to go make a sandwich. Because of this, developers had to be clever. In 1990, Microsoft bought a collection of symbols from three designers: Charles Bigelow and Kris Holmes. These two are legends in the typography world; they created the Lucida font family, which you’ve definitely used if you’ve ever opened a PDF.
They had originally designed these symbols as "Lucida Icons," "Lucida Stars," and "Lucida Arrows." Microsoft took the best bits of these three sets and mashed them together. They named the resulting Frankenstein font Wingdings. It was a play on "Windows" and "Dingbat."
It was a brilliant hack.
Since a font is basically just a set of instructions telling a computer how to draw a shape, a Wingding "image" took up almost zero space compared to a traditional graphic file. If you wanted a picture of a telephone in your newsletter, you didn't "insert an image." You just changed your font to Wingdings and hit the letter "Shift + 9." Boom. Technology.
The Lucida Connection
Charles Bigelow and Kris Holmes didn't just doodle these. They were meticulously crafted to match the weight and style of the Lucida typeface. This meant that if you were writing a professional document, the little symbols wouldn't look out of place or "janky" next to your text. They shared the same mathematical proportions.
Honestly, the level of craft in a font that most people use to make "secret codes" is pretty staggering.
Is it a Language? (No, but People Tried)
People often ask if you can "read" Wingdings. You can't. It's not a cipher. It’s a mapping system. In a standard font, the number 65 in the computer's brain represents the capital letter "A." In Wingdings, the number 65 represents a specific symbol—in this case, a victory sign or "peace" hand.
There is no linguistic logic to it.
The letter "A" isn't a hand because "A" stands for "Action" or something deep. It's just because that's the slot where the designers decided to put that specific vector. However, that didn't stop the world from losing its collective mind in 1992.
The NYC Controversy
Shortly after Windows 3.1 launched, a rumor started spreading like wildfire. People noticed that if you typed "NYC" (New York City) in Wingdings, you got a skull and crossbones, a Star of David, and a thumbs-up.
It was a PR nightmare.
Microsoft vehemently denied any malicious intent. They explained—repeatedly—that the placement of symbols was almost entirely random based on the original Lucida sets. To prove they weren't being anti-Semitic or hateful, when they released Webdings (a later version of the font) in 1997, they manually coded the sequence for "NYC" to be an eye, a heart, and a city skyline. "I Love New York."
Crisis averted. Sort of.
Then came 9/11. A new urban legend claimed that if you typed the flight number of one of the planes—Q33 NY—into Wingdings, it showed a plane flying into two towers followed by a skull and a Star of David.
Except it was a total lie.
Neither of the planes involved in the Twin Towers attacks had the flight number Q33 NY. Someone had just found a combination of symbols that looked scary and worked backward to invent a "prediction." It’s a classic example of pareidolia—our brains desperately trying to find patterns in random noise.
The Three Flavors: Wingdings 1, 2, and 3
Microsoft didn't stop at just one set. They eventually branched out because, apparently, we needed three different types of pointing fingers and fifteen types of arrows.
- Wingdings (Original): This is the one you know. It has the zodiac signs, the religious symbols, the gestures, and the basic office supplies like scissors and folders.
- Wingdings 2: Released with Microsoft Office versions, this one is much heavier on numbers. It has digits inside circles, squares, and weirdly specific clock faces.
- Wingdings 3: This is the "Oops, All Arrows" edition. If you need an arrow that curves, bends, or looks like it’s doing a backflip, this is where you go.
Why Do We Still Use Wingdings in 2026?
You’d think that in the era of 4K video and high-res emojis, these 1-bit style symbols would be dead. They aren't.
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They’re actually incredibly useful for UI (User Interface) design. When a developer is building a simple app, sometimes they don't want to load a whole library of SVG icons. They can just call up a character from a font that is already installed on 99% of the world's computers. It's fast. It's reliable.
Also, Wingdings paved the way for Unicode.
From Dingbats to Emojis
In the early days, if I sent you a document with a Wingding symbol, and you didn't have the Wingdings font installed, you'd just see a random letter. It was a mess.
This led to the creation of Unicode, a universal standard where every single character—whether it's an "A," a Kanji character, or a "Smiley Face"—has one specific number that every computer in the world recognizes. In a way, the goofy little "hand" symbol in Wingdings is the direct father of the 🖐️ emoji you use today.
How to Actually Use Wingdings (Without Looking Crazy)
If you're using them for more than just 90s nostalgia, there are a few "pro" ways to utilize these symbols in modern documents.
- Checkboxes: If you’re making a form in Word and want a box that people can actually see, Wingdings (specifically Wingdings 2) has much better-looking boxes than standard keyboard characters.
- Custom Bullets: Tired of the boring black dot? You can change your bullet points to any Wingding symbol. A little pointing hand makes a list feel much more "vintage" and intentional.
- Social Media "Hacks": Because some Wingdings characters were eventually absorbed into the standard Unicode set, you can sometimes find their equivalents to use in Instagram bios or Twitter names where standard "images" aren't allowed.
The Technical Limitation
One thing you've gotta remember: Wingdings is a proprietary Microsoft font.
If you're designing a website and you just type a letter and set the font to Wingdings, it might look great on your Windows laptop. But if a guy looks at that site on an old Linux machine or a specific type of mobile browser that doesn't have that font pre-installed, he’s just going to see the letter "J" instead of a smiley face.
This is why modern web design uses "Icon Fonts" like FontAwesome or Google Symbols. They work on the same principle as Wingdings, but they "carry" the font file with the website so it never breaks.
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What Most People Get Wrong
People think Wingdings is a "secret" font. It's not.
It’s just a shortcut. It’s a piece of 1990s engineering that was so efficient and so simple that it refused to die. It’s the digital equivalent of a Swiss Army Knife—maybe not the best tool for every job, but it’s always there in the drawer when you need a quick fix.
Next time you see a weird symbol in an old document, don't look for a hidden message. Just appreciate that some designer in 1990 sat down and meticulously drew a tiny pair of scissors so that you wouldn't have to.
Actionable Next Steps
If you want to play around with this pieces of history, here is how to find the "useful" stuff:
- Open the Character Map: On Windows, type "Character Map" into your search bar. Select Wingdings from the dropdown. This lets you see every symbol and the corresponding key without guessing.
- The "J" Trick: In the original Wingdings, a capital "J" is a smiley face, "L" is a sad face, and "K" is a neutral face. It’s the original emoji shortcut used by millions of office workers in the 90s.
- Check Your Mapping: If you are a developer, stop using Wingdings for web icons. Use SVG or a Google Font instead to ensure it doesn't render as gibberish on non-Windows devices.
Wingdings is basically a fossil. But it's a living one, and it's still doing its job thirty-six years later. Not bad for a bunch of tiny pictures.