His career in journalism began when, aged 24, he joined the Milan daily newspaper Il Giornale, headed by Italian journalist Indro Montanelli; he soon distinguished himself as a writer and became the paper's London correspondent.

For Il Giornale, in the period leading up to the fall of Communism, Severgnini worked as special correspondent from Russia, China and several Eastern European countries.

Following the failure of Montanelli's project at La Voce, Severgnini joined in1 995 the Corriere della Sera, Italy's biggest newspaper, for which he still is an op-ed columnist and an editor.

His most recent books are Off the Rail – A Train Trip Through Life (Berkley, New York 2019) and Neoitaliani (Rizzoli, Milan 2020), which will be published in 2022 in the US as Italian Lessons: 50 Things We Know About Life Now (Viking Penguin Books USA) Severgnini taught at the Walter Tobagi graduate School of Journalism at the University of Milan (2010–2020).

He has been a research fellow/writer in residence at MIT/Massachusetts Institute of Technology (2009), Isaiah Berlin Visiting Scholar at Oxford University (2013) and a visiting fellow at Ca' Foscari Venezia (2013); he has taught also at Middlebury College Vermont (2006), and at the universities of Milan-Bocconi (2003 and 2006), Parma (1998) and Pavia (2002), which elected him Alumnus of the Year in 1998 and 2011.