‘Sprezzatura’: The Art of Standing Out, Subtly

The art of effortless cool isn’t just for James Dean and the directors of Italian fashion houses. With the right attitude, any guy can summon a little ‘sprezzatura.’ Here we offer a critical investigation of the term, as well as some tips.

No one makes not caring look as good as the Italians. There's the architectural insouciance behind their world-famous leaning tower and the instinctual olive oil drizzle that transforms a piece of toast into a delicacy, but mostly it's the attitude of Italian gentlemen. They've got that effortless cool that’s tough to nail down. But of course, the Italians have not only pinpointed it, they’ve given it a name: ‘sprezzatura.’

Where did sprezzatura come from? At the beginning of the 16th century, nobleman Baldassare Castiglione penned The Book of the Courtier, a guidebook for distinguished gentlemen like himself. He argues that in addition to getting your art on (this was the Renaissance, after all), it was also important to make it look totally effortless. Sprezzatura was thus the “art that conceals art.”

Castiglione was writing for the nobility, of course, so sprezzatura in this case was less about attitude and more about etiquette. Defined in the Oxford English Dictionary as “studied carelessness,” its meaning and application today actually goes against the grain of Castiglione’s instructions to wear subdued colors and to “follow the prevalent customs of [one’s] surroundings.” Today it’s more about rakish style decisions that they come off as carelessness.

There are a few Italian guys who are crushing it regularly on the sprezzatura front. You see guys like haberdasher Lino Ieluzzi looking polished with a flicker of indifference, throwing a classic double-breasted suit off with an appealingly unruly pocket square. Or entrepreneur and man-about-town Lapo Elkann taking dandyism to new heights with fine tailoring in bold colors. Such stylish nonchalance is something Elkann might have inherited from his late uncle, former Fiat chairman Gianni Agnelli, who was known for the pleasant surprises he’d spring on his outfits, like a cropped tie or a watch worn over his cuff.

While we can learn a lot from these icons, the most important quality of sprezzatura as style philosophy is how personal it is. That loud shirt you’ve been contemplating or the unexpected detour you’re considering on a first date? If it feels right, it’ll probably look good.

A Beginner’s Guide to Sprezzatura:

  • Pair expensive style pieces with vintage finds. Even better are family hand-me-downs piece, like a grandfather’s tie bar, watch, or cufflinks.

  • Swap in some color where it is least expected. Your socks might be a good place to start.

  • Juxtapose the luxe with the shabby. Maybe that’s a bucket hat paired with a Saville Row suit. Or, a tube of Italian-imported Marvis toothpaste in a camping dopp kit alongside a cheap sawed-off drugstore toothbrush.

  • Wear accessories in unexpected ways. You might not be ready to wear a tie over a sweater, or a watch on top of your cuff, but you might try giving your tie knot a subtle twist and see how it feels.

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