The Complete, Unbeatable, Esquire Guide to Smart Casual Style in 2021

Paddy Maddison
·14-min read
Photo credit: Hearst Owned
Photo credit: Hearst Owned

Smart and casual: the yin and yang of putting your clothes on in the morning. On one end of the axis is you dressed in a top hat and tails on your wedding day. At the other, you in jeans and your best jumper, staggering down the hotel stairs to the morning after breakfast.

Or at least you did. Because in the last year, invitations have been on hold. No more weddings. No more fun. But, with the government announcing a roadmap out of lockdown, fun is back, and now is a better time than ever to prepare for the tricky smart-casual dress codes that'll be stamped above most events in the calendar.

Because it is hard, this smart casual business. It must contain elements of both in perfect balance, so that instead of fighting each other, they combine to create an outfit that adds up to more than the sum of its parts.

The trouble is, as brilliant as it is when handled correctly, smart casual remains one of the most misunderstood terms in the menswear lexicon. Removing your tie does not a smart casual look make. Nor does adding a suit jacket to jeans. Smart casual outfits are about balance, but just like a seesaw, getting the distance between each pole right is critical. Super smart with super casual is doable, but get a single detail wrong and you'll lose the equilibrium that makes the outfit work. Equally, if you go only-just-smart and only-just-casual, there's no tension. No fun. No individuality.

Much of the uncertainty stems from just how broad a concept it is. The smart casual dress code leaves a lot of room for interpretation and, by extension, a lot of room for anxiety and mistakes. Not what you need when stepping into that tricky second date, or even trickier second job interview.

But it doesn’t have to be difficult. With the right guidance and a little styling nous, anyone can make smart-casual work for them. Here we guide you through the pitfalls, offer you pro tips, and address the most common questions surrounding menswear’s most common – and yet most loosely defined – dress code.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

It'd help by answering the obvious: what exactly is smart casual? It's a query that's left countless men confused, and over (or under) dressed at the next function.

It's likely that the style first cropped up in the Fifties as a toned-down extension of business-casual. Not that a history lesson helps you actually figure out what it entails, but CONTEXT is important. Which is, perhaps, why smart casual is often misinterpreted in a very specific way, according to Joe Ottaway, a stylist that tends to David Gandy, among others.

“There’s an ongoing habit of some men to define smart casual as a shirt, tie, blazer, and jeans,” he says. “This is one of the biggest pitfalls to avoid. Instead, think of it as a contemporary extension of your classic smart wardrobe. Just invest in a few staple pieces that build on that idea, while offering maximum versatility.”

The other pitfall is exactly when to wear smart casual, especially since its meaning shifts depending on whether you’re at a christening or a works do. But according to Matches Fashion's head of menswear, Simon Chilvers, you just need to remember a couple of simple things.

“When’s the best time to wear smart casual? For a lot of men the answer is likely to be: most of the time,” he says. "Otherwise, it’s always a good idea when you’re going into unknown territory, but want to feel relaxed and confident.” In other words, think of it as your default setting. A sort of does-it-all uniform that you can bend and shape to fit in with your own personal style. In a sense, that's what it's always been. What’s changed over the last couple of decades is which pieces count as smart casual.

“With the suit-and-sneaker combo becoming more and more visible on the red carpet, the goalposts for what can be classed as ‘smart’ have shifted significantly,” says Chris Brown, freelance stylist and the creative force behind many of David Beckham’s most noteworthy looks. “Alongside high-end sneakers, the drawstring trouser is another example of how contemporary elements are creeping into the smart casual aesthetic. The key is about incorporating finer-quality clothes that are still casual, but also well fitted and rendered in premium fabrics.”

Think of the smart casual dress code as a contemporary extension of your classic smart wardrobe. Just invest in a few staple pieces that build on that idea, but also offer maximum versatility.

At its core, smart casual is all about looking put together, but not like you want people to comment on how put-together you look. It means making an effort, but not turning up in a three-piece suit. And ultimately, it’s about balance; a little bit of formal tempered with a touch of off-duty, to create outfits that average out somewhere in the middle. That doesn’t mean a tuxedo with trainers, but it does encompass laid-back details in 'smart' pieces, and dressier 'casual' pieces, then fusing them to create a look that blurs the lines between the two.

Six essential smart casual pieces

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Your first instinct is to grab the suit jacket. But not so fast, young gun. The rigidity and angularity of one of the most classic menswear pieces immediately puts you in the smarter end of smart casual. And, with a shirt and jeans, it's a little "dad, mum's not coming back" mid-life breakdown.

Of course, that's not to say they're totally out of bounds. Relaxed suits – those with a softer shoulder and a relaxed fit – are well slotted with a white T-shirt, or, if you fancy something a bit more fun, a Cuban collar shirt. The Italians often go for an unlined, shoulder pad-less blazer, and informal details like patch pockets and lighter fabrics can casualise your suit further. “Somewhere between a jacket and shirt, an unstructured blazer looks smart enough, but feels relaxed to wear,” explains Oliver Spencer, menswear designer and master of modern smart-casual style. “It’s a wonderful thing to have as part of your smart casual wardrobe.”

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Which brings us to the question of trainers. Once solely reserved to sports, then teenagers, then weekends, luxury's big embrace of the big sneaker has allowed for a rethink – as has the wider relaxation of dress codes at large. Maybe hang fire on the Gucci Rhytons. Instead, take a sole from menswear's swelling stable of high end, minimalist kicks, like Common Projects, or even an Adidas Stan Smith. “The minimalist sneaker is basically the Derby shoe of the new millennium,” says Chilvers. ‘It’s a discreet, acceptable-to-most piece of footwear that goes with anything and everything.”

Keep simplicity front of mind when shopping for these key pieces, says Chilvers. “They should be tonal, without much obvious branding or fussy details. If you were describing this shoe to a friend you’d use the following adjectives: timeless, dependable, comfortable and versatile.”

Photo credit: Hearst Owned
Photo credit: Hearst Owned

The Oxford shirt is the very definition of smart casual. “It’s the epitome,” says Olie Arnold, style director at Mr Porter. “It’s one of the few structured shirts that takes on a clean-cut appearance when tucked in, and an easy-going nature when left untucked. It’s the perfect hybrid, and classic whites and blues have long been wardrobe staples.”

Thick fabric gives the Oxford shirt a relaxed edge when compared to finer dress shirts, while the collared design keeps things smart. All of this works together to make this one of the most versatile and reliable smart casual pieces in your wardrobe.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

More relaxed than leather Oxfords, yet more refined than a sneaker, the suede Derby is a smart casual shoe that sits perfectly between those two extremes. “It’s a must-have smart casual item,” says Ottaway. “A classic all-rounder, perfect for dressing down a suit or for elevating a pair of jeans or chinos.”

As with most footwear, a pair of suede Derbies is an investment piece, and something it’s worth splashing out on in the long run, according to Ottaway. “I’m a firm believer that you can create a strong, timeless wardrobe without spending a fortune on clothes. However, when it comes to shoes, it is really important to invest as much as you can in a quality pair.”

Photo credit: Hearst Owned
Photo credit: Hearst Owned

When there’s any doubt about whether or not denim is too casual, chinos are the way to go. These preppy stalwarts come in all shapes and sizes, but where smart casual dress codes are concerned, a classic, slim fit is never the wrong choice.

“The beauty of a pair of slim-fit chinos lies in their versatility,” explains Daniel Johnson, luxury personal shopper and stylist. “They can be styled any way you wish: cut high on the ankle with a turn up for a modern touch, or with a quarter break for a more traditional style. Colour-wise, beige and navy are the traditional choices, but I’d recommend getting a pair in grey and you'll be making your outfit choices with ease.”

Photo credit: Hearst Owned
Photo credit: Hearst Owned

A decade ago, the only job interview at which it was acceptable to wear drawstring-waisted trousers was also one where you had a whistle around your neck. These days, things are different. “Sitting somewhere between track pants and smart trousers, drawstring trousers have seen a surge in popularity of late,” says Spencer.

This new breed of laid-back legwear offers all the comfort of a pair of jogging bottoms, but with the sharp cut and smart looks of a pair of tailored pants. Perfect for dressing up everyday pieces like plain T-shirts and minimalist sneakers, this hybrid garment is a true cornerstone of modern smart casual style.

Six smart casual style tips

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Adding in a smattering of sportswear is a simple but effective way to give your smart casual style a 21st century update. That’s not to say you should show up to your next office party wearing an Aston Villa shirt tucked into your suit trousers; instead, mix low-key athletic pieces, like polo shirts, tailored joggers and leather sneakers, with relaxed tailoring staples. This is where that unstructured blazer becomes your sartorial superhero.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

It's easy to stick to tried-and-tested standbys when navigating a smart casual dress code, but making it your own is all about letting a bit of personality shine through. Which does not mean carte blanche to wear magic-eye-puzzle pocket squares and novelty cufflinks. To really make an outfit sing, step outside the confines of traditional accessories and allow yourself some creative freedom. Who says you can’t wear a fisherman beanie with tailoring? Boring people, that’s who.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

A lot of men play with silhouette when trying something new with their wardrobe, but unexpected fabrics can be even more impactful. Texture is the secret to advanced style – it gives depth, contrast and all the good stuff that turns an outfit from humdrum to humdinger. Think cable knits, corduroy, suede and mohair, all of which will make staple pieces more interesting and inject some individuality into failsafe smart casual ‘fits (it's a lot easier to pull off than colour or pattern, too).

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Every bit as pivotal as texture, colour can completely alter the mood of an outfit. If you want to nudge things towards the smarter end of the spectrum, then darker tones are generally dressier, which makes them particularly good for giving off-duty pieces like bombers or jeans an on-duty feel. In the same way, brights pull things more casual. That’s not to say you should reach for raspberry chinos, but a mustard shirt will give tailored looks a relaxed air.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

The world’s best-dressed men are all experts in layering, and it’s particularly effective for smart casual looks. Provided it’s not the height of summer, think in threes (not including outerwear), which is the the magic number for creating that all-important sense of depth. Case in point: a fine-gauge knit between an Oxford shirt and blazer transforms a default pairing, as will a collarless gilet between a rollneck and overshirt. When it does warm up, an unbuttoned shirt of a tee adds a louche, Fifties feel. Don’t be afraid to get creative.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Wearing a smart watch with casual outfit used to be a sartorial misstep on par with brown in town. Fortunately, no one cares about those rules any more, which means your timepiece can be as much of a dress code-definer as your sneakers or blazer. Anything that falls in the expansive grey area that separates a dress watch from a field watch is a good place to start, but it’s particularly difficult to go wrong with a good diver or chronograph. Aside from that, consider the strap. A canvas NATO if you’re thinking laid back, or a bracelet for any time a little more refinement is required.

Smart casual style icons

Photo credit: Getty Images
Photo credit: Getty Images

If you’re ever feeling uninspired in the face of a smart casual invitation, take a style cue from Hollywood’s king of casualwear. When he’s not mixing earthy tailoring and vibrant shirts on the red carpet, Gos can be found blending workwear favourites and smart casual staples to create a look that’s instantly recognisable as his own. It’s a glorious thing to behold and one of the many reasons he should be your first man when it comes to borrowing a few menswear moves.

Steal these moves

  • Don’t disregard workwear. A well-placed denim jacket or pair of worker boots can lend some Gosling-approved ruggedness to an otherwise uptight outfit.

  • Smart casual is often about removing extraneous details, but as Gosling proves, some well-deployed jewellery – a simple medallion, a sleek dress watch – can nudge your look toward either the smart or casual end of the spectrum.

Photo credit: Getty Images
Photo credit: Getty Images

He may be known for his role as villain Erik Killmonger in Black Panther, but when it comes to style, Michael B Jordan is one of the good guys. With a knack for fusing the trend-led with the classic, Jordan uses smart casual staples – think rollneck knits and Chelsea boots – to balance more fashion-forward pieces. A sucker for slick outerwear, Jordan knows how a good coat can transform a look. So should you.

Steal these moves

  • Invest in a proper, smart overcoat, preferably made from wool and in a neutral colour. That way, you can wear it across most of your smart casual wardrobe. You’ll find it lends even the most haphazardly conceived outfits an air of refinement and purpose.

  • Pick a palette and stick to it. Jordan isn't one for tie dye, but he understands the way that sky blue pops beneath navy. It's all about creating points of difference that lift your entire look, without overwhelming it.

Photo credit: Getty Images
Photo credit: Getty Images

If you’ve ever looked in the mirror and asked yourself, “Am I too old to wear this?”, just ask Idris Elba. If he’s doing it, take that as a green light. He’s on-trend and fashionable, but avoids anything he wouldn’t want to stumble across in a Facebook Memory. His secret? Simplicity. Elba’s smart-casual looks are fuss free, streamlined, modern and, a lot of the time, composed of nothing more than a knitted polo, dress pants and a pair of luxe leather sneakers.

Steal these moves

  • While his smart casual outfits are often simple, the one detail that really makes them stand out is perfect fit. Get to know your local tailor.

  • Little flourishes – like high-top trainers, colourful beanies or rugged leather flight jackets – stand out more when what's around them doesn't compete for attention. It's the best way to make less look like more.

Photo credit: Hearst Owned
Photo credit: Hearst Owned

Ryan Reynolds knows how to nail everything from a three-piece suit to a T-shirt and trainers, but it’s that middle ground where he really excels. The Deadpool star is a master of using smart and contemporary pieces to compliment one another, whether it be a slimline bomber jacket and dress pants, or white minimalist sneakers and a suede jacket.

Steal these moves

  • Invest in a core selection of light outerwear that can be used to add a touch of class to basic outfits. Think suede bombers, wool overshirts and unstructured blazers.

  • Remember the power of texture. You can stick to simple, neutral colours but still create outfits with depth by contrasting tactile fabrics like denim, suede and flannel.

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