The four fonts at a glance
All four are symbol fonts. You type ordinary keys, and the font draws a picture instead of a letter. They differ in age, in the kind of pictures they hold and in where you will find them installed.
- Wingdings. Released by Microsoft in 1992. Office and computer items, pointing hands, faces, religious symbols, zodiac signs and check boxes. Ships with Windows, from Windows 3.1 up to Windows 11.
- Wingdings 2. Part of the same Microsoft family, with no separate release year from Microsoft. Pointing hands, numbers in circles, fancy ampersands and interrobangs, check marks, crosses and geometric shapes. Not on the Windows 11 font list; it came with Microsoft Office.
- Wingdings 3. Also part of the Wingdings family, again with no separate release year from Microsoft. Almost entirely arrows and triangles, plus symbols for keyboard keys. Not on the Windows 11 font list; it came with Microsoft Office.
- Webdings. Designed in 1997. Web and interface icons such as media player buttons, plus buildings, landscapes and vehicles. Ships with Windows, from Windows 98 up to Windows 11.
Wingdings and its two siblings
Microsoft's Wingdings family page explains where the fonts came from. Kris Holmes and Charles Bigelow drew them in 1990 and 1991 as Lucida Icons, Lucida Arrows and Lucida Stars, to go with their Lucida text fonts. Microsoft renamed and reorganized the set and released it in 1992 as Wingdings. The purpose was practical: pictures of a PC, a monitor, a mouse, a printer, folders, mail and a wastebasket for the new graphical interfaces, alongside pointing hands, arrows, stars and ornaments for bullets.
The same page lists three files, Wingding.ttf, Wingdng2.ttf and Wingdng3.ttf, and shows the original Wingdings in every version of Windows from 3.1 on. Microsoft does not give Wingdings 2 and Wingdings 3 their own dates. Wikipedia's Wingdings article dates both to 1990 and says they were distributed with Microsoft Office up to version 2010, not with Windows itself. That matches Microsoft's Windows 11 font list, which includes Wingdings and Webdings but neither of the numbered fonts.
The three split the work. Wingdings is the general one, with a bit of everything. Wingdings 2 leans toward document marks: check marks, crosses, ballot boxes, pointing hands and the numbers 0 to 10 in white and black circles. Wingdings 3 is the arrow font, with arrows in many weights, directions and styles.
Webdings, the web font
Webdings came later and from a different team. Microsoft's Webdings page says it was designed in 1997 for web designers who wanted a quick way to put graphics on a page: a font scales cleanly and loads faster than a pile of image files. It was a joint project between Microsoft's Vincent Connare, the designer of Comic Sans MS, and the Monotype designers Sue Lightfoot, Ian Patterson and Geraldine Wade.
That purpose shows in the symbols. Webdings has window buttons and media controls on the number row, then buildings, landscapes and vehicles on the letters. Microsoft added it to its core fonts for the Web in June 1997 and lists it in Windows from Windows 98 onward.
The same sentence in all four fonts
The easiest way to see the difference is to type one sentence and change only the font. Here is "Meet me at 8" in each of the four.
- Wingdings💣︎♏︎♏︎⧫︎ 🔾︎♏︎ ♋︎⧫︎ 🖰︎
- Wingdings 2🖣︎🙚︎🙚︎⓿︎ ④︎🙚︎ 🙦︎⓿︎ 🖸︎
- Wingdings 3⮍︎🢫︎🢫︎◀︎ 🡖︎🢫︎ 🢧︎◀︎ ⮠︎
- Webdings🏔︎📦︎📦︎🛲︎ 🕴︎📦︎ ✔︎🛲︎ ⏩︎
Even this short line shows each font's personality. In Wingdings, the capital M is a bomb (💣︎) and the lowercase e is the Scorpio sign (♏︎). In Wingdings 2, the same M is a hand pointing down (🖣︎). Wingdings 3 turns it into a curved arrow (⮍︎), and Webdings makes it a snowy mountain (🏔︎). The 8 becomes a computer mouse, an optical disc, another arrow and a fast forward button.
Across the 94 printable keyboard keys of all four fonts, only one symbol repeats: the circled backslash (⦸︎), which is capital X in Wingdings 2 and lowercase x in Webdings. Everything else is unique to its font, so you cannot read a Webdings message with a Wingdings chart.
Which one should you pick?
It depends on what the symbols are for.
- A secret message or an Undertale reference: Wingdings. It is the original of the family, and Gaster's text in Undertale uses its capital letters. Use the Wingdings translator.
- Check marks, crosses and numbered lists: Wingdings 2, with its ballot boxes and circled numbers. Try the Wingdings 2 translator.
- Arrows, or a puzzle that is hard to guess: Wingdings 3. Its symbols are nearly all arrows, so a message looks like a pattern rather than pictures. Use the Wingdings 3 translator.
- Playful messages that read like little scenes: Webdings, with its houses, buses, planes and boats. Open the Webdings translator.
- A Word document someone else will open on Windows: Wingdings or Webdings, since both are on Microsoft's current Windows font list. A reader without Microsoft Office may not have the numbered fonts.
Copying the symbols as text
A font only works where it is installed. Paste Wingdings text from a word processor into a chat app and it arrives as plain letters, because the font does not travel with the text. Unicode changed that in 2014. A Unicode report on Wingdings and Webdings tracked how all 867 symbols from the four fonts would be handled, and Unicode 7.0, released in June 2014, added many of them as real characters.
The translators on this site use those Unicode characters, so the symbols you copy stay symbols when you paste them into a chat or a post. They do not use or offer Microsoft's font files. Each device draws the characters with its own fonts, so shapes can look a little different from Word. When the exact look matters, save the message as an image.