Menswear, along with fashion in general, underwent a hard reset in 2020. For obvious reasons that we are all tired of hearing about, we were forced to reassess our approach to clothing and style on both an individual and collective level. Out of this reassessment, we only came to a consensus on two ideas. One is that comfort will no longer be sacrificed in the name of fashion; it is now a primary consideration whenever getting dressed. The other is that there are no rules or overarching trends dictating the course of menswear right now. Previously disparate fashion niches have all been blended together by designers and individuals alike. The thing is that this disregard for the rules in the name of comfort and self-expression has existed for decades in the Italian sartorial philosophy of sprezzatura. 

In the 1950s and 1960s, young Italian gentlemen started wearing traditional menswear in a more relaxed manner. Shirts were halfway unbuttoned, blazers were rumpled, pocket squares were haphazardly stuffed into breast pockets, suit jackets and pants were mismatched, and designer scarves were loosely draped over the shoulders. It was a way for men to demonstrate that they had great style while simultaneously refusing to constrict themselves with conventional rules. It was a punk attitude wrapped up in tailored clothing.

The history of sprezzatura

The earliest known use of the word sprezzatura appears in a 1528 book…