The Art of Not Trying: Sprezzatura in Menswear

Why effortless style can’t be forced

A while back, I had a conversation with someone who told me their approach to clothing was sprezzatura. I found that interesting for a number of reasons. First off, I completely understood what they meant. Don’t get me wrong—it’s a brilliant way to dress. But should it really be an approach?

Yes, sprezzatura is a look, but the moment we focus too heavily on it, we lose what makes it work in the first place. It’s like the idea of being cool—the second you try to be cool, it’s instantly uncool. The same applies to sprezzatura; the more effort you put into cultivating a “studied nonchalance,” the more forced it becomes.

The term sprezzatura originates from Baldassare Castiglione’s The Book of the Courtier, published in 1528. Castiglione describes the ideal courtier as someone who moves through the world with effortless grace—never appearing strained or overly studied. He defines it as:

“A certain nonchalance, so as to conceal all art and make whatever one does or says appear to be without effort and almost without any thought about it.”

At its core, sprezzatura wasn’t about fashion. It was about presenting yourself in a way that seemed completely natural, even if great skill or preparation was behind it. The best example might be a skilled orator—someone who speaks so fluidly that you’d never guess how much practice went into their delivery.

Over time, though, sprezzatura has been absorbed into the menswear world and taken to mean something slightly different.

In modern menswear, sprezzatura often gets reduced to a series of stylistic choices—unbuttoned shirt collars, wrinkled blazers, or mismatched ties. These details, while sometimes effective, can feel like they’re trying too hard to look effortless. And that’s where the essence of sprezzatura gets lost.

It’s about being at ease in your clothes, not because you’ve planned it that way, but because it’s simply how you feel. The best examples of sprezzatura don’t announce themselves; they just are.

I think sprezzatura should be more of an idea—something to influence you, but not something you should actively seek. The best way to approach it is to simply run loose with it. Wear what you want. Let it come naturally.

Part of what I find appealing about sprezzatura is how it influences the way you take care of your clothes and how you present yourself. I mentioned in my last blog about breaking rules that Oxford shirts shouldn’t be ironed—they should be allowed to wrinkle. That’s a small example of what sprezzatura is all about: accepting those little imperfections that make the look feel more real.

One thing I personally enjoy, and that I think lends itself well to the sprezzatura look, is combining a really smart top half with a worn, battered pair of sneakers. There’s something about this contrast that feels effortless and grounded, especially when those sneakers have seen years of use.

I’ve got a pair of Supergas I’ve had for years—they’re so worn in, and that’s what I love about them. Paired with a crisp shirt, they give off a sort of worn-in collegiate vibe that feels natural and unforced. It’s a look that says you’re comfortable with where you are, and that’s the heart of sprezzatura.

It’s hard to give examples of sprezzatura without accidentally turning them into rules. The reality is, there are ways you can get closer to the look, but honestly, I wouldn’t recommend trying to chase it. The best way to embody sprezzatura is to simply wear your clothes well, wear them in, and let it come naturally. The more you learn from what’s in your wardrobe, the more you’ll figure out what works and what doesn’t. That’s when sprezzatura finds its way into your style—without you trying to force it.

Now, let’s take a look at a few examples where I think style is actually working, where the person hasn’t outright claimed to have that sprezzatura look, but it’s there nonetheless.

Someone who immediately comes to mind when I think of the idea of Sprezzatura is Jason Jules.

Everything he wears just seems to work. He never copies—you can see his influences—and while Ivy certainly plays a major part in Jason’s wardrobe, he always adds his own flair to the look. Rolled-back cuffs, a ring, his signature round-framed glasses, and knits tied around the waist. Jason looks like he just naturally pulls everything off—that, to me, is the epitome of sprezzatura.

I’ve been scrawling through my Instagram trying to find other people who I think embody this idea too. Someone who also possesses that artful ease is illustrator Dick Carroll.

You may know Dick from his brilliant Ivy-inspired comic strips, packed full of garments, funny anecdotes, and the odd style tip or two. For me, though, Dick’s sense of style always comes across as effortless. In the picture above, his magazine acts as an accessory, the pen in his pocket adds a layer of interest, and his collar—popped out over his jacket—gives a laid-back charm. Intentional? Maybe not. Is it sprezzatura? Definitely.

Here’s another example I came across on Instagram by danmpantoja. I love the outfit he’s put together here. The contrast of smart with casual layers works as an excellent juxtaposition that I’m fully on board with. I love the small but powerful details—the pen and sunglasses in his pocket, the unbuttoned shirt, and the slightly loose tie. This look teaches us that you may be wearing beautiful clothes, but it’s how you wear them that counts.

---

Trying to teach someone the art of sprezzatura is like trying to teach comedy—you can’t teach someone to be funny. They have to be immersed in that world, not even realising they’re being funny. Sprezzatura works in a similar way. It’s not something you can force or deliberately try to master. It’s a process that happens almost by accident. The key is not overthinking it.

I know it’s not the greatest advice, but just trust that it’s going to happen when you stop trying so hard. The only bit of advice I’d give is not to care too much about what you’re wearing. Just stick it on, and let it fall into place.

The only rule should be no rules.