In the age of the iGent and Pitti Uomo, the casual elegance known as sprezzatura has become the Holy Grail for stylish men. But can the pursuit of casual elegance go too far and become simply outlandish? In this article, we’ll explore the limits of sprezzatura.

What Exactly is Sprezzatura?

Though it has been associated with the resurgence of interest in menswear fueled by the internet, the Italian word sprezzatura is actually quite old. It was first used by Baldassare Castiglione (1478-1529)  in The Book of the Courtier, a classic of Italian Renaissance literature. Castiglione’s aim was to instruct noblemen on proper manners and comportment, and part of that was cultivating an elegant style while appearing natural and unrehearsed about it, whether in dress, dance or speech. He called this “a certain nonchalance, so as to conceal design and make whatever one does or says appear to be without effort and almost without thought.” Several centuries later, Castiglione’s concept of sprezzatura in dressing was taken to its greatest extremes by the infamous Beau Brummell, who supposedly spent hours in front of a mirror each day arranging his cravat to make it look like it was done with no effort at all. For Castiglione and Brummell, avoiding affectation in favor of sprezzatura was the absolute first rule for being a gentleman, an idea that seems to be upheld by those who relentlessly pursue it today.

Italian Sprezzatura and the Idea of Imperfection

During the last half-century or so, the practice of sprezzatura has focused mostly on the idea of imperfection or incongruity, inspired by the style of Italian industrialist Gianni Agnelli, who wore his wristwatch over his shirt cuff or his back tie blade longer than his front one. Agnelli consciously cultivated what can be seen as odd stylistic errors with outfits that were otherwise formal and correct. This emphasized a rakish personality and projected a lack of self-absorption in his appearance. Perhaps these little touches suggested he was too busy with business to be fastidious about his dress and was too important to care; maybe wearing hiking boots with a suit made him appear more accessible to the public even though he was the quintessential capitalist tycoon. Certainly, nowadays when anything but casual clothes can be perceived as a sign of pretension or vanity, displaying the imperfections of sprezzatura is a way to declare that you reject elitist dress codes while still dressing up. Sprezzatura is popular, especially among younger men, because it represents a sort of visual rebellion, not only against snooty traditions but against the monotonous business wear of office drones. Ironically, many sprezzatura converts spend a considerable amount of time and a conscious effort to look unconsciously casual.

Agnelli watch

Agnelli boots

The Dangers of Sprezzatura

Adopting sprezzatura doesn’t come without risks. However you dress, you create certain impressions, so it’s important to know where you can go wrong to avoid the chance of committing a stylistic faux pas.

1. It has its time and place

First of all, recognize that sprezzatura is meant for specific situations: you can’t wear loafers without socks when attending the Queen’s Garden Party in Buckingham Palace. The same applies when you’re in court or climbing the corporate ladder. Sometimes, you need to follow the rules and dress codes unless you want to risk negative consequences for the sake of a stylistic statement.

2. Keep it low key

It’s also possible to go too far and end up looking ridiculous and contrived, so restraint is still the name of the game.  Today, sprezzatura tends to look more like the flamboyant style of Agnelli’s grandson Lapo Elkann than Agnelli himself. The incongruous elements are too numerous or so over the top as to be obvious efforts to get attention while sacrificing style, elegance and grace. In addition, if you display too many examples of sprezzatura, those who are unaware of the concept may think you just look sloppy while those who do understand it know you are trying hard, so it becomes insincere. Adopting one example of rule breaking while being well dressed is a good starting point. Do it regularly so that it becomes natural and associated with your style.

Lapo Elkann

3. Try to be original

Lastly, sprezzatura is accomplished best when one’s nonchalance is unique, graceful and original. Following the examples you see in photos of Pitti Uomo can, therefore, become its own kind of conformity, and people will know it. When Agnelli did his thing, he was unique, but with thousands of people doing it on Instagram, we end up with the impression that everyone is copying Agnelli. It becomes an obviously self-conscious move, the total opposite of what sprezzatura should achieve. That being said, it’s fair to acknowledge that it is not easy to come up with a truly original take on sprezzatura these days; our best advice is to find something that appeals to you and wear it with confidence.

To be frank, it has become difficult to pull off sprezzatura without criticism these days because the concept has been promoted so much online. I’m reminded of a particular photo of George Wang, the owner of menswear boutique Brio Beijing, in which his shirt collar has folded back. He took it upon himself to declare that it wasn’t intentional to avoid being called out for a calculated sprezzatura, but commentators still expressed disbelief. So, remember the first rule is not to look like you’re trying too hard. The second rule is to not deliberately seek attention while feigning innocence of your own calculated style choice.

Brio owner George Wang in a Permanent Style profile showing a folded collar.

Ways to Do Sprezzatura

Now that you have a sense of the guidelines and principle of sprezzatura, let’s take a look at different ways in which men have tried to achieve it and whether these are successful. Ultimately, you can decide which approaches you find appealing.

1. Leave Buttons and Buckles Undone

A rare moment of British Royal sprezzatura. Prince Charles with an open double-breasted blazer (and a glass of Pimm’s).

Many sprezzatura moves simply involve not fastening things. Perhaps the easiest and most natural is to leave your suit jacket or sport coats unbuttoned. Formal rules of dress call for you to button up whenever you are standing, but nothing says nonchalance like ignoring this. If you are wearing a double-breasted jacket, the move is even bolder. An open jacket allows you to showcase your shirt and tie, and, even though an appropriate fit is always best, leaving a jacket open can disguise fits that are either too tight or too loose. It will also hide the collar gap that appears with many off-the-rack jackets if one of your shoulders is lower than the other.

Collar Gap

On a shirt, you have several unfastening options. One is not to button your shirt cuffs. Lino Ieluzzi of Al Bazar in Milan is known for doing this with double cuffs, but barrel cuffs would be more subtle. This probably looks best in summer, when the relaxed mood and need for ventilation make it seem practical rather than calculated.

Lino displaying sprezzatura – sunglasses, open shirt cuffs, wristbands, ring, sunglasses, cigarette, jacket on the shoulders, sleeve cuff buttons undone

A popular move online is wearing a button-down collar but not buttoning down the points. I am personally not a fan of this, as the buttons are more visible but hardly ornamental. If you have a nice collar roll with a long button-down, unbuttoning destroys it. Opening just one collar button is even worse because it creates an unbalanced look, though it does look more like you accidentally forgot to button up.

button down

Interestingly, leaving your top shirt button undone while wearing a tie has never caught on among the style aware, maybe because it is so commonly done on television by beleaguered police captains or FBI agents to show some small rebellion against authority. It’s meant to convey that even though they’re in positions of authority they’re still hard-working blue-collar guys who only wear a tie because they have to, something a stylish gent would not agree with.

FBI agent Seely Booth, on the TV show Bones, often wore his top shirt button open with a loosened tie.

For the bottom half of your outfit, you could try leaving one buckle undone if you wear double monk strap shoes. Especially if you have to unstrap to put your shoes on, this might be an easy next step. It’s fairly subtle, though when I tried it, my buckles jingled as I walked–making it quite unsubtle in the end. This also trended on the internet recently, so it could be seen as calculated. I haven’t seen shoelaces left untied yet, but I bet you can imagine next year’s Pitti peacocks tripping as they pose for photographs this way.  Thankfully leaving things unfastened below the torso has not extended to leaving one’s fly open as a form of sprezzatura, though, with the internet penchant for the new and outrageous, we may see it when people run out of other ideas.

Bespoke Dudes Fabio Attanasio wearing the back buckle open

2. Play Around with Your Necktie

Ties are the most visible opportunities for sprezzatura, and it can be achieved in a variety of ways. The simple act of using an asymmetrical knot like the four-in-hand as opposed to a more ordered, symmetrical knot, such as the half-Windsor, will be more nonchalant. It may be tempting, especially if you are just getting into tailored style, to want to try a bunch of complicated knots like the Merovingian, but the fact is that the many elegant gentlemen use only a four-in-hand. The more artful and elaborate the tie knot, the more it shows conscious concern for dressing, which is the antithesis of sprezzatura. If you want to experiment with knots while maintaining an unpracticed air, try another asymmetrical knot like the Victoria or Nicky.

A second widespread sprezzatura technique is never to use the keeper, the loop on the back of your front tie-blade that holds and hides the narrower end of your tie, something that Sven Raphael Schneider also recommends. When you let the thin back blade of the tie hang loose, so it can be seen, the tie seems less formal. It’s especially good to make a narrower tie look wider, as the blades overlap. I, personally, like the two blades to be close together and dislike seeing them split widely to form a large flyaway V across my shirt because it appears unkempt, but some men prefer that look.

Not using the keeper allows you show the back blade of your tie. Also notice the folded collar.

On the subject of tie blades, Agnelli was known for occasionally having his back tie blade longer than the front. This happens accidentally if you don’t adjust the length of your tie blades properly before tying your knot, so it can seem like a natural form of indifference–you made a mistake and left it like that. I don’t like to do it because it’s too apathetic for my taste and seems a conscious imitation of “l’Avvocato.”

Some men defy convention by wearing their neckties too long. The standard rule for proper tie length is to ensure that the tip ends just above your waist. However, wearing it considerably longer is a sprezzatura move, provided both blades are loose; otherwise, a single arrow dangling right over your crotch just comes across as vulgar. A tie that hangs long can happen normally if you wear high-waisted pants, if you are shorter than average, or if your tie has stretched, though some purposely buy long ties to create the effect.

tie blade tucked in

A variation is to tuck the longer tie into your waistband. I tend to be more conservative and have never gotten used to the long tie look, though tucking it in would be more appropriate.

3. Wear Your Belt Long

Since we’re talking about the waistline, a belt can also be used for sprezzatura, specifically wearing one that is too long on purpose, just like a tie. The usual rule of sizing is to buy a belt one size larger than your waist measurement, such as a 36 if you have a 34-inch waist. However, some men go up two to three sizes and let the excess material at the tip hang down. This is actually a signature style of cashmere king Brunello Cucinelli. The result is even more obviously a phallic projection, like a Renaiss

Sprezzatura Do’s and Don’ts

ance codpiece, that is best avoided as gauche. If a hanging belt is ever done, it would be with totally casual looks like jeans and a tee shirt.

belt too long

4. Mix the Casual and Formal

Cucinelli is also known for wearing jeans with a tie and formal double-breasted jacket, similar to Agnelli’s work boots with a suit. These blends of casual and formal are characteristic of sprezzatura, and how to do this could be the subject of its very own article, but for now, we can say that chinos and jeans will generally work best with an unstructured sport coat, one that already has casual elements, like patch pockets, not flap, and a natural shoulder rather than a lot of padding. Footwear should probably tend more toward the formal–like double monks or derby shoes rather than sneakers, though the choice depends on your individual sense of what looks appropriate. Note that sneakers and a suit rarely look stylish together.

Cucinelli wearing jeans with jacket

5. Choose Materials and Styles That are More Relaxed

The Neapolitan-style jacket with unpadded shoulders is itself perfect for sprezzatura because it’s less rigid (literally) and formal than its British counterpart. In general, select styles that are less business appropriate but still tailored.  For example, you might choose an unlined, untipped tie instead of a lined one, a cutaway or button-down shirt collar instead of a standard spread–the Ivy style is, after all, a comparable form of rebellion.  Similarly, certain fabrics project the desired unpretentious vibe more than others. A wool-silk-cotton blend sports coat is more sprezz than the standard worsted wool worn on the job. Shantung silk, grenadines or knitted ties are likewise better choices than printed silks. Try to envision the sartorial equivalent of distressed or antiqued furniture, something that has a comfortable beauty.

6. Don’t use Elaborate Pocket Square Folds

Beau Brummel may have toyed with his cravat for hours to get an unpracticed appearance, but the equivalent of this today would be creating a natural look with your pocket square. As with tie knots, you can find instructions for an abundance of elaborate pocket square folds. Yet, the more artful and complex the folds get, the further you move away from the principles of sprezzatura. A sense of nonchalance is obtained first by gathering up your pocket square and shoving it into your breast pocket, then by turning, twisting and fluffing it randomly until it looks pleasing yet arranged by chance.  Consider the beauty of a cloud in the sky as it randomly changes shape. Sure, there are occasions for the neatness of a classic fold or the arranged points of a crown fold, but if you feel like sprezzatura, rely on crumpling and stuffing your pocket square.

Puff fold with pocket square by Fort Belvedere

7. Relax Your Grooming

Lastly, as an extension of being more nonchalant in dressing, you can also be less fastidious with your grooming. This doesn’t mean abandoning the use of deodorant or letting your nose hairs hang out but rather something like showing stubble instead of going cleanly shaven or leaving your hair long and slightly tussled rather than neatly cut and combed.

Conclusion

In the nearly 500 years since the concept was developed, the nature of sprezzatura has certainly changed. Despite this, it should never be seen as an excuse for slovenliness or as a means of getting attention through over-the-top violations of stylistic rules. Nor should it ever become mere slavish imitation. However, if you adhere to the core ideas of sprezzatura you’ll be able to inject a bit of Italian rakishness into your classic style. Only you can decide how much or how little sprezzatura makes sense for your style.

Which sprezzatura approaches do you agree or disagree with? How far do you take it? Share your perspective in the comments below.