Dealing with fashion from an educational perspective may seem like a contradiction in terms as fashion has always been considered a vacuous and superficial issue. However, fashion exerts a great influence in the contemporary world, especially digital, inhabited by influencers and bloggers who "dictate fashion" in terms of customs, habits and languages. Treading with pedagogical wisdom in the streets and highways of social and digital relationality can allow us to intercept interesting connections between fashion, digital infrastructures and new languages to set up an active and new pedagogy in our era of increasingly sudden cultural changes.