Smart casual dress codes are quite frankly a nightmare. For many it conjures images of chinos, R. M. Williams and a poorly ironed Oxford shirt. But what if we told you it was possible to nail the oxymoron of ‘smart’ yet ‘casual’ while still giving yourself enough room for personal expression? 

In years gone by, smart casual had its rigid set of rules. Guides on menswear forums loved nothing more than suede derby shoes, bomber jackets and button-down shirts—and while those pieces can still be worked into an outfit, the rules of the game have changed, largely in that, they are more relaxed than ever. Instead of a defined formula of Chelsea boots, tan slim-fit chinos and a suit jacket, men are more often than not finding that ‘smart casual’ is more of a feeling rather than something that can be captured with a sort of paint-by-numbers approach. 

Of course, there still needs to be an emphasis on looking ‘smart’ and not underdoing an outfit, but there also have to be elements of casualness. This can be achieved with two approaches: dressing an outfit up or dressing an outfit down.

Let’s look at the first example. Say your standard style leans pretty casual. You’ve got a pair of jeans that fit really well, a crisp white T-shirt (or even a singlet) and some nice smart casual shoes like boots or loafers that work with jeans as well as they do with a suit—wardrobe staples that most men should have already. Taking that base and throwing on a nice double-breasted unstructured blazer over the top will dress the outfit up and add a little bit of formality, giving you an excellent balance. 

Likewise, taking the base of a suit and making some smart decisions with your footwear or how you style your neckline can be a game changer. Chris Pine is a pro at this, turning an otherwise quite stuffy country club vibe, unbuttoning a bit, and swapping smart black shoes and a belt for a more casual vibe. 

Alternatively, someone like Shai Gilgeous-Alexander comes out smart casual from a completely different angle, taking a borderline faux pas Canadian tuxedo and adding a slim black tie to elevate the whole look from cowboy to NBA player who means business, but isn’t afraid to get dirty. And hey, if you can channel that attitude with your smart casual outfits, we would say that you are winning. 

Smart casual attire can be a tough nut to crack—but with practice and an understanding of which of your everyday items can be elevated by some smart casual pieces, and vice versa, you’ll be able to develop your own personal take on a conundrum that has been facing men for the better part of three decades. Need some inspiration? Below, find examples of seven men who nailed the smart casual dress code with ease and flair. (As an aside, these looks can also be a great base for business casual, but maybe just tone them down a bit if your office isn’t so creative.) 

Jacob Elordi

Aussie actor Jacob Elordi has burst onto the scene thanks to his breakout role as Nate in HBO’s Euphoria, but as much as he has become a star for his acting chops, he has also become one for his clear grasp of style. In recent months, he fashion moves have included everything from mixing tiny handbags and bare feet to full-on shorts with a suit. And what these apparent style contradictions show, is that Elordi has a very strong grasp of how to create a good outfit by mixing and matching pieces that you wouldn’t normally see together. This makes him a perfect dresser for smart casual style.

Take the above look. Elordi could have easily taken most of these pieces and styled them in a different way—add a tie, dress pants and voila it’s a cocktail look—but by leaving the top button open on his collared shirt and going for a pair of faded blue jeans, the look becomes much more casual, transporting the sporty jacket from boring country club to the night club. 

Austin Butler

Austin Butler, like Elordi, has enjoyed a spectacular ascent into the limelight of not just Hollywood, but also style. Unlike Elordi though, Butler is a lot more formulaic with how he approaches his outfits and as such, he is an excellent source of inspiration if you are simply looking for a uniform approach to building out your smart casual wardrobe. The key to emulating Butler’s smart casual style? A good double-breasted blazer. 

If you take a geeze at Butler’s personal style over the past few years, he has three levels and they all revolve around good jackets. First, is his full casual mode: workwear jackets, jeans and boots. Then up top, he can go very formal in a double-breasted suit with a tie, bow tie or even a ribbon from the neck. But, when he goes smart casual, he combines the two, eschewing what you would typically think of as ‘smart casual’ shirts in favour for T-shirts and singlets, but still keeping the double-breasted blazer that has become his hallmark. It’s a surefire style move and one that you can easily copy for yourself. 

Tyler, the Creator

A touch more avant-garde with his personal style, Tyler, the Creator has nonetheless essentially perfected the art of uniform dressing with a smart casual bent. If you take anything away from Tyler’s style let it be the power of a good pair of loafers and a well-placed tie. As he has proved time and time again, taking an outfit that traditionally wouldn’t be formal at all—brown pants and a puffer jacket, for example—but pairing it with some nice chunky loafers and throwing on a flamboyant tie adds the perfect amount of formal spice to get you over the line. If you are a confident dresser already, this is the man you want to emulate.  

Chris Pine

Despite being one of the most well-established actors on this list, it is only in recent years that Chris Pine has really started dressin’. In the past year alone, Pine has run the gamut from casual to smart casual to formal almost as well as any other man in the limelight. He plays with colours, cuts and styles effortlessly and is someone that you should definitely be looking to right now as a guiding light for not just smart casual dressing, but general style. The lessons to take from his smart casual style? Undo some buttons, add some colour and if in doubt, throw the jacket over the shoulder. 

A$AP Rocky

Looks like fatherhood has changed the OG fashion killa as A$AP Rocky is dressing like a grown-up more often than not these days. Trading sneakers for suits and caps for ties, the rapper has stepped up his game in order to keep up with his partner Rihanna. In recent months, Rocky has nailed the brief by consistently going for a baggier cut of suit and often pairing it with jeans and cowboy boots for a casual twist on a regular suit. We’re not saying anyone can match Rocky on the style front, but hell, you can still learn from the best. 

Andrew Garfield

Andrew Garfield has certainly had a glow-up since he broke through as Peter Parker back in 2012 when The Amazing Spider-Man dropped. These days he is also a perfect man to follow into the abyss of smart casual style. Whether he is donning knit polo shirts or getting funky with a flowy satin shirt and jeans (as you see in the above image), Garfield constantly takes regular smart casual silhouettes and elevates them with interesting style moves. Even if you don’t want to attempt something as advanced as the above look, the idea—relaxed jacket, jeans and loafers—is still something anyone can nail. 

Shai Gilgeous-Alexander

The only athlete on this list, Oklahoma City Thunder star Shai Gilgeous-Alexander has been pushing the style envelope since he broke into the NBA a few years ago. Typically going all out in wild fashion looks, SGA occasionally tones it down and has given us some excellent examples of how to do smart casual in 2023. This dressed-up Canadian tuxedo is a key example of how you can take a look that normally wouldn’t work for a more formal event and touch it up with a tie to fit the dress code. After all, the man is the most stylish player in the NBA for a reason. 

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