Indeed, Windsor is really a pet favorite in the world of bootleg merch. It’s been used a few times in drops from Boot Boyz, the sly sorta-streetwear brand that turns midcentury academic totems into advanced fashion. Windsor is also literally in the logo for Jam, a brand helmed by the artist and designer Sam Jayne. Jayne likes the font because of its quirkiness—it has a “hand-drawn human element to it.” He uses it all the time in his other career, as a graphic designer. When he started Jam, using Windsor was a natural decision: it had personality.
Perhaps Windsor has blown up because of what it doesn’t represent: the streamlined minimalism of big tech. To signify its future-facing approach, Silicon Valley companies have historically turned to Swiss Modernism, a design movement responsible for Helvetica, that simpler-than-simple typeface that you can find both in the New York City subway system and the Microsoft logo used from the ‘80s up until the early 2010s. Windsor, on the other hand, looks hand-drawn and cushy, in direct opposition to sleek, Silicon Valley minimalism. If using Helvetica is like sitting in an Eames chair, outfitting your band’s poster in Windsor is like lying down on a shag carpet while wearing nothing but a pair of velvet bell bottoms. Stephen Coles, the editorial director at the San Francisco-based Letterform Archive, calls it “the corduroy of fonts.”
Coles explained that Windsor, and fonts like it, often emerge in response to trends in minimalism that are coupled with new technology and waves of modernization. He puts the cycle at about every 50 years. Windsor was first developed by the Stephenson Blake foundry in 1905. It came out of the Arts & Crafts movement, which originated in England during the rise of industrialization. Art & Crafts designers worried that machine production would destroy craftsmanship. The movement had socialist underpinnings, and valued the individual’s ability to beautify the world and the home. If you look at it the right way, Windsor’s deliberately handcrafted aesthetic appears nearly anti-capitalist.
While Windsor was first created in response to fears of over-industrialization, it reemerged in the ‘60s and ‘70s, alongside concepts like eating a macrobiotic diet, kibbutz living, and a general frustration with Man in the Gray Flannel Suit-era capitalism. As well as appearing in the Whole Earth Catalog, Windsor showed up on quite a few record covers, and appeared on an iconic, early pro-Angela Davis poster. It was also, obviously, used a fair amount in advertising—perhaps its most infamous usage from the last 50 years is in the title cards for Woody Allen films.
Windsor’s reappearance in the last few years makes plenty of sense. It’s been 50 years since it last saturated the market. Big tech cynicism is at an all time high. A striking number of young Americans identify as socialists.
Ultimately though, nobody has ownership over a typeface. For every Whole Earth Catalog-style publication with Windsor on the front cover, there was also a cigarette company using the font. In 2021 there are plenty of funky bootleg t-shirt designers and craft beer companies using Windsor, but it’s also used in derivative formats to get you to buy Chobani. We’re already headed in the direction where Windsor is so overused that people are starting to get sick of it. One can only have too much of a good thing, if you even want to call it that. Soon it will probably disappear—if only for fifty years or so. Windsor has a way of coming back.