What on earth is that man doing with his tie? Has he dressed in a huge hurry? What’s with the collar sticking out? Hold fire with your assumption that the subject of your disdain just doesn’t know how to dress well. Those points you critique may, in fact, be expressions of ‘sprezzatura’, the art of dressing artlessly. At least seemingly so…

But why would anyone seek to do this? For one, in a world – and in the culture that is clothing – that loves a rule, sprezzatura brings a touch of rebellion, it’s a style hack without going full on punkish revolution. It’s also a means to signal your individuality, even though you’re still perhaps wearing conventional clothing. Most of all, those who can carry off sprezzatura – and in attempting so it’s a fine line between style king and style clown – win the prize of being cool.

Like ‘cool’, you know a touch of sprezzatura when you see it. Like ‘cool’ too, it can be overdone, at which point it’s not cool any more. But, and here’s the good news, it can also be attained – acted out until it’s natural. And, as the writer Thom Gunn said in in his poem on the young Elvis Presley, “whether he poses or is real, no cat bothers to say…”

What Is Sprezzatura?

Sprezzatura is a way of getting dressed that undermines the accepted way of dressing, while still adhering to its typical garments.

If a tie is usually worn so the narrow side of the blade is behind the wider part, it’s sprezzatura to wear it the other way round; if the end of a belt is usually tucked into a belt loop, it’s sprezzatura to leave it dangling; if fastening a tailored jacket is what counts for good dress etiquette, it’s sprezzatura to leave it undone. Of course, to now do these things is not sprezzatura – you need to find your own touch of distinction.

Street Style, Pitti Uomo 94Street Style, Pitti Uomo 94

Yes, it all looks a bit convoluted, especially for a way of style that is meant to convey the complete opposite: a lack of caring. But then sprezzatura, right back to its 16th century beginnings, was always something of a performance: a performance of personal panache.

The History Of Sprezzatura

‘Sprezzatura’ is one of those Italian words which, like ‘focaccia’ or ‘linguini’ seems alien at first, and then just becomes a natural part of your vocabulary. Unlike ‘focaccia’ or ‘linguini’, however, defining the word is akin to the trouble with defining ‘cool’ (in the non-temperature sense). Everyone knows what it is, but that’s not enough to say what it is; and if you think you have it, you haven’t.

The idea of sprezzatura, however, predates the commonplace use of ‘cool’ by about 400 years. It was in 1528 that writer and royal hanger-on Baldassare Castiglione coined the word in his book The Book of the Courtier – effectively a self-help tome for those wanting to climb the greasy pole of life ruled by the whims of aristocracy.

The book was a best-seller, a blockbuster, in its day. It proposed or, more accurately, repurposed ancient ideas of the ideal, Renaissance Man – he would be shaped by the best ideas; he’d be the ‘strong and silent’ but he would also have this thing called ‘sprezzatura’, which also referred to his appearance.

Marcello Mastroianni, 1960Marcello Mastroianni, 1960

In terms of style, sprezzatura suggested the kind of man who looked effortlessly elegant – though never stuffy or overly formal. The key word was ‘effortless’: it all looked easy and unforced, as though the man in question just happened to look simultaneously together and laid back, as if by accident. Sprezzatura was, if you like, faking it to make it. As Castiglione suggested, the more we work at practicing the principles of urbanity, the more they become part of you.

Whilst the Brits tried it as early as the 19th century, it was the Italians who made the most of it. “Historically it’s central to the idea of style in Italy,” notes Alessandro Sartori, the artistic director for Ermenegildo Zegna. “You see that in, say, the readiness to blend formal dressing with sportswear, in the play with textures – matt next to shiny. There’s always a way of dressing too Italian that slips into stereotype – that very polished look – but sprezzatura is much more organic.”

What Sprezzatura Means Today

Dress codes continue to break down; the lines between formal and casual dress are ever more blurred; we wear sneakers to work and a suit to go out. If ever there was less need for sprezzatura – a means of standing out without, you know, standing out – now might seem to be it. But, in fact, with the tendency to look ever more alike all the time, arguably there’s a greater need for a personal style to shine through in the details. Add with today’s greater accessibility of menswear – in terms of fashions, variety, pricing, ideas – it becomes a matter less of what you’re wearing as the way you wear it.

Marcello Mastrioanni, the actor, claimed, as he once said, “to hate fashion. Fashion and designer labels… It’s all so stupid for people to pay all these high prices just to have the designer’s name in a coat”; and yet he ordered 12 bespoke suits from Vittorio Zenobi, his tailor in Rome, every year. Capturing some essence of sprezzatura of cutting against the grain, he once noted that “the day when everyone is very, very elegant, I will start to go around dressed like a tramp.”

Giovanni AgnelliGiovanni Agnelli

Fellow Italian Gianni Agnelli, of the family behind the Fiat car-making dynasty, similarly embodied sprezzatura for the 20th century. He would wear his button-down collar unbuttoned; he wore his watch over his shirt cuff; he always wore his tie just a little off-centre and a little undone; he’d wear his double-breasted suits undone (a sartorial faux pas); he’d leave a couple of his suit’s cuff buttons undone; he’d sometimes wear slippers or hiking boots with his tailoring, creased though it was, albeit perfectly creased. He broke the usual sartorial expectations and didn’t worry about it.

Street Style, Pitti Uomo 92Street Style, Pitti Uomo 92

Certainly, listed like that, the quirks of sprezzatura dressing may seem somewhat contrived, as though the individual in question was trying to be willfully different. And there is an element of truth to that. “But give an Italian man the same clothes to wear as one from Germany or the UK, for example, and he will still find a touch of difference,” reckons Naples shoemaker Paolo Scafora. “It’s why you can go anywhere in the world and spot an Italian man a long way off. He is expressing his self-respect and his respect for others.”

Express Yourself, Sprezzatura-Style

Commitment

Lapo Elkann in MilanLapo Elkann in Milan

Sprezzatura is a look or an attitude you have to embrace; it can’t be done just a bit, without conviction, because then the effect is to look unfinished, or scruffitura, as the Italians never called it. The overall look is a bit ‘just got out of bed’ – albeit a bed in a five star hotel in the Amalfi Coast with nothing to do but soak up the admiring glances.

Rough And Ready

Street Style, Pitti UomoStreet Style, Pitti Uomo

Think semi-formal – unstructured jackets, textured fabrics, knitted rather than silk ties – and the almost distressed. Foxing – the wear around a shirt collar – the scuff of a shoe, the patina on a belt, can all add to sprezzatura’s key lack of stiffness.

Let It All Hang Out

Street Style, Pitti Uomo 94Street Style, Pitti Uomo 94

If it can be undone, consider undoing it – except your shoelaces and trouser fly. But a top shirt button (with tie), and a shirt or suit cuff, are all fair game. Leave tailored jackets open. And avoid ironing – at least nothing more than a light press.

It’s Not Just About Tailoring

James DeanJames Dean, 1955

It’s harder to do because there are fewer elements to play with, but sprezzatura can apply as much to casual dress as more tailored dress. Take James Dean in Rebel Without A Cause for example: he’s in jeans, white T-shirt and a bomber jacket, but the jacket is worn just so, fastened only at the bottom and with collar turned up. Sprezzatura can see the smart and casual happily intermingled.

Discover Your Signature

Street Style, Pitti Uomo 94Street Style, Pitti Uomo 94

Find a way of wearing that you like – the way Agnelli wore his watch or his shirt collars – and stick with it so that, over time, it becomes a signature. But just one or maybe two such signatures will do it. Don’t do all that you could. Then, to the unknowing eye, sprezzatura just looks messy. It needs, in an ideal world, to be your signature too – not, ahem, something you read about somewhere… But this is easier said than done.

Sprezzatura Dos and Dont’s

Do…

Understand there’s a time and place for sprezzatura – it works perfectly in a creative setting, less so in those in which tradition dictates a high degree of formality. Sprezzatura is not for the wedding – especially if you’re the groom – or for the boardroom, ever.

Avoid slipping into the stereotype of Italian dressing: very fitted jackets, ankle-skimming trousers, highly polished shoes and so on. Sprezzatura may come from Italian culture (technically before Italy existed) but it is not about looking Italian.

Be prepared for some not to get it. It might only take a few random comments from people reminding you that you’ve forgotten to fasten the buttons on your Oxford shirt collar, or that your tie isn’t straight, for the fun to wear off really fast. Still lost? Take your cues from the masters below and you’ll be on the right track.

Don’t…

Overdo it. The 21st century Italian peacock – of the kind documented in street style shots from the likes of the Italian menswear fair Pitti Uomo – does not have sprezzatura, for he lacks restraint, subtlety and, often, taste. Sprezzatura is, in contrast, all about little details, and less is more with those.

Think too hard about it. If it doesn’t come naturally, arguably it’s best just not to go there and to stick with the tried and tested, socially accepted notions of dressing well. Make too much of it and there’s a risk of being called out; and self-conscious sprezzatura is not sprezzatura at all.

Key Sprezzatura Figures

Alessandro Squarzi

The Italian fashion entrepreneur – he oversees the marketing and distribution of a number of brands – is well-placed to dip into various styles. And yet his year-round trademark is a pair of white trousers, which has never been easy to pull off, but which – in true sprezzatura mode – he stays loyal to regardless.

But his overarching skill is to make basic, comfortable clothing look incredibly stylish. He’s well into T-shirts and sweaters, slippers and sneakers, with some vintage bits thrown in – the likes of some old Levi’s or a throwback jacket. 

Alessandro Squarzi

Brunello Cucinelli

The founder of the Italian luxury lifestyle brand that goes by the same name, Cucinelli at first appears to rock standard Italian peacockery: the ankle-skimming trousers, the pocket square, the silky scarf. But he has an in-built scruffy edge that makes his look just a little off, and so much cooler for it – a jacket is crumpled, or worn over a crew-neck sweatshirt; a sharp double-breasted blazer is teamed with ripped jeans and a long belt; or a jacket and trousers that should be parts of a suit, but are actually ever so gently mis-matched.

He still looks very Italian, of course. But it’s his take on Italian. And that’s not easy in Italy.

Brunello Cucinelli

Johannes Huebl

Is the German model an example of sprezzatura? His characteristic style is about as simple, as classic, as conservative as it comes, which leaves little room for individuality. He’s big on wearing one dark shade head to foot.

But then, on occasion, he surprises: a white – white! – double-breasted blazer that somehow he can wear without looking like the maitre’d; a shirt untucked; a hefty scarf tucked into his sweater; and some little touches – a brightly-coloured tassel on some dark loafers.

Johannes Huebl

Joe Ottaway

The menswear consultant and style advisor to David Gandy gets top marks simply for being frequently seen alongside the model – and we mean seen; he doesn’t disappear into the shadow of those cheekbones. That’s because he’s doing his own thing (and he’s remarkably tall).

That thing is essentially rather olde English: three-piece suits, watch chains and nice monk-strap shoes. But he’s playful with colour – albeit within the classic menswear palette – and isn’t afraid to look just a little bit poncey. A suit, T-shirt and broad-brimmed hat combo? A belted pin-stripe safari jacket, worn with sleeves rolled? It’s not for everyone. But he wears it well.

Joe Ottaway

Key Sprezzatura Pieces

Unstructured Blazer

A tailored jacket with all the padding and lining taken out perfectly embodies the notion of sprezzatura. It’s comfortable, non-restrictive and allows the wearer to give off a sense of nonchalance that’s hard to achieve with a sharp, structured garment.

Whether double- or single-breasted, wear yours open and undo a couple of the cuff buttons on each sleeve for a touch of sprezz.

The Best Unstructured Blazers For Men

BOGLIOLI Storm-Blue Unstructured Suit Jacket - click to buycos WOOL SEERSUCKER SUIT JACKET - click to buysuitsupply HAVANA GREY PLAIN blazer - click to buyreiss BOSTRUS DOUBLE BREASTED BLAZER - click to buy

Knitted Tie

The most casual type of tie, if there is such a thing. Although not suitable for the boardroom, knitted ties are ideal for smart casual attire and, as they lack stuffiness, give the potential to be worn with plenty of sprezzatura.

When tying it go for a simple four-in-hand knot, but don’t fuss around in the mirror for ten minutes adjusting and re-tying multiple times. Instead, just tie it once into a tight knot and roll with it – if the rear blade hangs longer than the front then so be it.

The Best Knitted Ties For Men

t.m.lewin Navy Knitted Silk Tie - click to buyt.m.lewin Navy White Fleck Knitted Silk Square End Tie - click to buycharles tyrwhitt Burgundy silk slim knitted classic tie - click to buyRUBINACCI 5cm Knitted Silk Tie - click to buy

Pleated Trousers

Comfortable, smart and far less common than their flat fronted cousins, pleated trousers are here, and they’re here to stay. Usually designed to sit higher on the waist, they have the potential to elongate your legs and can look extremely elegant when worn well.

Slightly more formal than regular trousers, try rolling the cuffs to offset this and wear with suede loafers, or, contrast the look completely with white sneakers. Sprezzatura is all about mixing the formal with the casual, after all.

The Best Pleated Trousers For Men

h&m Elasticated cotton trousers - click to buyuniqlo MEN RELAXED ANKLE LENGTH TROUSERS - click to buyALBAM Parachute cropped cotton trousers - click to buyUNIVERSAL WORKS Tapered Pleated Slub Cotton And Linen-Blend Trousers - click to buy

Button-Down Shirt (Worn Unbuttoned)

This is one of those things that can look contrived but, nevertheless, is a key sprezzatura detail.

First pulled off by Agnelli in the ‘60s – and by countless Italian followers since – leaving a button-down collar unbuttoned only works if it looks as though you were too busy, or just didn’t care enough to button it when you threw it on in the morning. If the rest of your outfit is too polished, you’ll just look affected.

The Best Buttoned Down Shirts For Men

suitsupply LIGHT BLUE STRIPE SHIRT - click to buyt.m.lewin Stretch Casual Fitted Pink Plain Button Down Collar Shirt - click to buydrake's Blue Chambray Regular Fit Cotton Shirt - click to buyJ.CREW Slim-Fit Button-Down Collar Cotton Oxford Shirt - click to buy

Pocket Square

Fewer men are finding a need for pocket squares nowadays – they’re often an unnecessary fad in a menswear world of tracksuits and limited-run sneakers.

But, for a sprezzatura-inspired look, they can add wonders to a suit. The pop of colour from your chest pocket can be your point of difference; just remember not to match your tie and just throw it in there and go.

The Best Pocket Squares For Men

suitsupply BROWN POCKET SQUARE - click to buyDRAKE'S Polka-Dot Silk Pocket Square - click to buyt.m.lewin Burgundy Pin Spot Silk Wool Pocket Square - click to buyreiss WILLIAM FLORAL PRINTED SILK POCKET SQUARE - click to buy