Is It ’Cause I’m Cool / Why You Dress Like Me is It Honesty or You Just a Fool

“I’m cool … / That’s cool … / He/She’s the coolest ...:” exclamations like these have described various types of elements: names, things, cities, characters, in a constant search of novelty and more à la page, more exciting and, of course, more niche. Who is cool is unique, unrepeatable but with a lot of imitators who sublimate the image and reverberate through many different means of communication: from the traditional to the contemporary, from the mass media to the most elite channels. But what identifies a person, a product, or a city as cool? Is it a strategy? Is it marketing or a spontaneous attitude? Is it one of these things or a combination of them? Starting from this assumption and from some emblematic case studies from the worlds of fashion, art, music, and in general all the creative fields (from the Marchesa Casati to Frida Kahlo, from Anna Piaggi to Miuccia Prada, from the “presence” of John Galliano and Maurizio Cattelan to the “absence” of Martin Margiela and Banksy, from Virgil Abloh’s multitasking attitude to Alessandro Michele’s conceptual retro-aesthetics, from Tamara de Lempicka’s “being cool and famous strategy” to the analysis of the trends’ life cycle, from the movie parodies of Totò (the Neapolitan actor) to Steve Jobs’s cool-nerd aesthetics and the design of contemporary new icons, this paper intends to investigate the roots behind the construction of coolness. This is a concept, that to be long-term and broadly resilient and not to be lost in “the long tail” of niches and subcultures, requires, now more than ever, solid cultural foundations and distinct elements wisely mixed.