The hidden language of symbols: decoding the mystery of Wingdings

Countries & Cities · Published 12 October 2026 Swipe more like this →

In short: To the uninitiated, it is a chaotic jumble of arrows, stars, and skulls. But for decades, this Microsoft typeface has been at the center of conspiracy theories, accidental antisemitism, and even indie game lore. Discover how a collection of simple glyphs became a vessel for unintended meaning.

Developed in 1990 by Microsoft, Wingdings is a TrueType dingbat font that replaces standard letters with various symbols. The original set was created by combining glyphs from Lucida Icons, Arrows, and Stars—elements licensed from designers Charles Bigelow and Kris Holmes. While the font has been a staple of Microsoft Windows since version 3.1, its arrangement has often sparked intense scrutiny.

One of the most enduring controversies involves the rendering of 'NYC'. Shortly after the release of Windows 3.1 in 1992, observers noted that typing 'NYC' produced a skull and crossbones, a Star of David, and a thumbs-up gesture. This led to accusations of an antisemitic message targeting New York City's Jewish population. Microsoft denied any intentionality, maintaining that the glyph arrangement was largely random. In contrast, the later Webdings font featured an intentional 'I Love New York' tribute, using an eye, heart, and skyline.

The font's symbolic power extends into modern pop culture and digital folklore. In Toby Fox's indie game Undertale, the character W. D. Gaster communicates using the typeface, specifically during Lab Entry #17. The font has also been the subject of post-9/11 conspiracy theories, such as claims that the sequence 'Q33 NY' represented the first plane to hit the Twin Towers. However, records show the actual flight numbers were AA11 and UA175, with tail numbers N334AA and N612UA.

Beyond the original set, Microsoft expanded the family with Wingdings 2 and 3. Wingdings 2, developed by Type Solutions, Inc., includes 16 forms of the index and various geometric shapes. Wingdings 3, also released in 1990, focuses almost entirely on arrow variations and symbols for keytops as defined by ISO/IEC 9995-7.

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