Like many great startup origin stories, the one for Love Billy!--a New York-based direct-to-consumer clothing brand--begins at a party. It was 2015, there really was a Billy, and Candice Pool Neistat thought it'd be funny to wear a T-shirt emblazoned with his name for his birthday. She found iron-on felt letters just like those her mother used in the 1980s. And a logo for a booming business was born.

Love Billy! is far from the only such company going retro when it comes to the crucial task of choosing a font. A slew of buzzy startups--including Glossier's extra-saturated Glossier Play, home-goods company Buffy, and Great Jones, which markets a line of colorful cookware--are doing the same. All of which represent a notable antithesis to the starker sans-serif letterforms ubiquitous among well-known, carefully designed DTC brands from Warby Parker to Outdoor Voices, and nearly all big tech firms (think: Uber and Facebook).

"Food and cooking are all about warmth. We want Great Jones to convey that," says co-founder Sierra Tishgart, who, with business partner Maddy Moelis and Emily Oberman of design studio Pentagram, came up with the logo design, specifically to shoot for something different. For years, "this clean, simple, 'no bones about it' typography was part of startup culture," says Oberman. But now? "It's about embracing joy. It's about wearing it on your sleeve, and not being afraid to be weird." 

The Old School

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A. Tyler Haney's ultra-hot company uses the OV Gothic font--which has a clinical look that the new breed are rebelling against. 

B. Millennial beauty giant Glossier smartly plays off its minimal logo with a much more sensual approach for its new cosmetics line.

C. Another Pentagram creation, the logo for this bedding startup is a slight reworking of the Cooper Black typeface.

D. Pentagram's Oberman tweaked Cruz Swinger for the Wing's playful-yet-classy logo.

E. This Bookmania-inspired font explicitly references vintage cookbooks and the "Thank You for Shopping With Us" bags from the late '70s.

F. Old-fashioned iron-on letters inspired this logo, which immediately communicates joy and wit.