The Best Smart Casual Dressing Guide You’ll Ever Read

Trying to find the true meaning of the phrase smart casual can quickly turn into a nightmare. The Oxford Dictionary defines it as “neat, conventional, yet relatively informal in style, especially as worn to conform to a particular dress code”. But these days it’s quite common for smart casual to be the dress code.

So you go online to search for smart casual style guides that variously counsel everything from shorts, which don’t strike us as especially smart, to Ascot ties, which don’t come over as particularly casual. And as the latter indicates, many of these guides feel like they were set in stone shortly after the ten commandments. Whatever smart casual means, it’s likely to be something different today than it was in the starch-collared 19th century.

“Smart casual is destined to be one of those terms that history will not be kind to,” says Josh Sims, author of Men of Style. “Thankfully, the recent explosion in non-designer-y brands offering considered, very wearable clothing is making moot the second guessing of whatever the term means. Because actually, it’s all quite smart now – but in a comfy way.”

The History Of Smart Casual

The precise origin of smart casual is as hard to track down as its meaning. Website The Phrase Finder – as definitive as that is – claims that the term is “thought to have originated around the 1980s” but was in “common use throughout the last century”. In fact, the first recorded usage of the terms dates back to a 1924 edition of Iowa newspaper The Davenport Democrat And Leader (although that was in relation to sleeveless dresses, which we certainly can’t advocate wearing).

Whatever the truth, it’s a fair assumption that smart casual is related in some respect to business casual, and the two are often used interchangeably, even though they’re different: one is for at work, and one isn’t. But back in the day, you didn’t just dress smartly to go to the office, but everywhere else too. As the traditional standards of dress eroded, smart casual was the hastily erected bulwark against total sartorial chaos.

“Smart casual suggests a transitional period between dressing up – that’s to say, more formally – and dressing down with the comfort and self-expression that more and more men are looking for,” says Sims. “The term also suggests a kind of panic among ‘authorities’ – restaurant managers, event organisers – as to how to handle the shift, so they’ve gone for some halfway house: dress casually but, you know, not too casually, please. The result? Endless confusion. Or men in blazers and open-neck business shirts.”

Don’t be those guys.

What Smart Casual Means Today

Smart casual means nothing, so it can mean anything. According to Mr Porter’s Style Advice page, the smart casual gamut comprises “pretty much anything smarter than a tracksuit, but less formal than a suit”. Thankfully, and rather more informatively, Mr P adds, “An ideal answer is a blazer, white shirt, neat jeans, and brown loafers.”

There is no one answer, though. In a well-meaning attempt to clarify that ironically complicates matters further, Debrett’s Guide for the Modern Gentleman draws a distinction between “formal smart casual” and “informal smart casual”. Formal smart casual is “a jacket or blazer, flannels, needlecord trousers, or chinos (not jeans), a shirt with a collar (not a T-shirt) and smart shoes (not necessarily lace-ups, but not trainers or sandals)”.

Informal smart casual remains vague, however, beyond consent for “smart, clean, dark-coloured jeans”, a pronouncement that “polo shirts are better than collarless T-shirts” and an instruction to “change from what you have been wearing at home”.

But while it might sound obscure, this last point is perhaps as good as any to start from. Part of the reason that smart casual is so hard to define is that it can mean radically different things in different contexts. It’s a state of mind as much as dress.

Smart Casual Style Tips

Change Your Attitude

“Smartness is more a matter of the appearance of your clothes rather than their style,” writes Sir Hardy Amies in A-Z of Style. “Shoes polished, trousers pressed, and tie properly tied are necessary factors in a smart appearance.”

The operative words here aren’t ‘shoes’, ‘trousers’ or ‘tie’ (we’re talking about smart casual, after all), but ‘polished’, ‘pressed’ and ‘properly’. A pristine T-shirt, indigo jeans and box-fresh trainers can look dressier than a wrinkled shirt, stained trousers and scuffed shoes.

A T-shirt, jeans and trainers won’t always be appropriate, mind. But smart casual is arguably more a mood or attitude than it is a set formula or combination of pieces. As Debrett’s says, “Just because an event is informal, it is not synonymous with making no effort.”

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Play A One-Two

As we’ve established, smart casual is nigh-on impossible to define. So a more helpful and practical approach is to start with a casual outfit and then change one – or better, two – pieces for smarter alternatives.

For example, take a bomber jacket, T-shirt, jeans and trainers. All very casual, right?

Now swap in any one of blazer, shirt, trousers or chinos and shoes. You should be verging on smart casual territory. Swap in two and you should be bang on target. Swap in three and, depending on the circumstances, you might even be too smart. It’s a fine line.

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Throw Some Shade

You don’t even have to change pieces to adjust the casualness of an outfit. Darker colours skew more formal, so smartening up can be as simple as turning down the lights.

For example, take an olive green bomber jacket, white T-shirt, stonewashed jeans and white trainers.

Now swap the olive bomber for a navy one, and the stonewashed jeans for indigo. Suddenly it feels dressier. Even more so if you swap the white T-shirt for, say, mid-grey or charcoal, and the trainers for navy or black.

The constituent styles are exactly the same, but the overall effect is very different. And the reverse is true: lightening up is a dimmer switch for smartness.

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Take The Rough With The Smooth

Another (major) factor that affects the relative smartness or casualness of a piece is texture. If you think about the most formal items in menswear – worsted wool business suits, say, or barathea dinner jackets – they’re almost invariably smooth and shiny.

Swap the worsted wool for a matte flannel or tweed, however, and you both literally and metaphorically change the feel of the piece. This will also often make the garment seem larger in size, which only adds to the more casual vibe, given that smarter looks are usually sleek and streamlined.

This is a handy rule of thumb and forefinger that you can apply to casualise much any piece: shirts, knits, trousers, even shoes.

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Blazer Trail

As previously mentioned, throwing a blazer over T-shirt, jeans and trainers is as easy a move as any to nail smart casual. But not all blazers are created equal: gold buttons are, to borrow a delightful phrase from Debrett’s, a bit “gin and Jag” (AKA the sort of middle-class people who drive Jaguar cars and drink gin and tonics).

As also previously mentioned, a blazer with some texture will rub up the right way with jeans. As will one cut a little shorter, perhaps also with slightly slimmer, more contemporary lapels. Patch pockets – which look like they’re stitched on – are similarly ‘cazh’.

Finally, ripping out the padded shoulders and canvassed chest found in smart blazers will also make them feel more casual, not to mention comfortable. N.B. Don’t actually rip your blazer, just look for the word ‘unstructured’.

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Button Up

A T-shirt can qualify as smart casual, provided that it’s plain, good quality, well-fitting and not washed to death.

But upgrading to a polo shirt will instantly smarten a casual rig. The buttons and collar put it further along the spectrum towards a shirt, but it’s still sporty. Indeed, as the name suggests, it was originally worn for playing polo, as was the button-down collar so that it didn’t flap around.

Which brings us neatly to the button-down shirt, which isn’t as stiff as one with a rigid collar and cuffs. It also commonly comes in fabrics such as Oxford cloth or chambray, which are less smooth and shiny.

Then there’s the grandad shirt. Collarless equals more casual. Capiche?

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Put On Your Finery

A jersey sweatshirt or hoodie wasn’t an element of our example outfit. But substituting a fine-gauge knit in merino, cashmere or even cotton for these thick, casual and sporty pieces can lend a soupcon of sophistication. Pull a plain jumper or cardigan over your T-shirt (and maybe swap the trainers for shoes) and you’re getting weaving.

Clearly a chunky knit isn’t going to have quite the same effect, although a shawl-collar cardigan instead of a jacket can look smart if it doesn’t have toggles or a massive moose on it. A knitted blazer is somewhere between the two.

A word or 23 on roll necks: too thick and they’re not smart, too fine and they’re about as casual as Hemingway’s drinking.

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Pocket The Difference

Legwear is usually a smart casual sticking point. For the most part, jeans are perfectly acceptable – even in a business context – as long as they’re dark and undistressed. But there’s always a risk. Then there’s failsafe chinos – emphasis on ‘safe’.

Your pins are an oft-missed opportunity to not formalise an outfit, but also flex. Going back to the bomber jacket, T-shirt, jeans and trainers example, swapping the jeans for tailored trousers can not only look smart, but also fashionable.

A textured, not-too-shiny fabric like flannel or linen can help you pull the casual trouser off, but it’s not an entry-level swerve. Which is why most guys stick to jeans or chinos.

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Toe The Line

As with jeans, there are few casual settings nowadays where you can’t get away with trainers. But if you’re in any doubt, then play it safe. As Debrett’s puts it: “The right shoes can rescue even the worst fashion disaster – the reverse is hardly ever true.”

What makes a smart shoe more casual? Colour: black is smartest, brown is more casual and tan more casual still. Silhouette: a round or almond toe is more casual than a pointy one, as is a chunky sole. And texture: nubby, matte suede is more casual than smooth, shiny leather.

For those reasons, wingtips, Derbies, loafers, Chelsea boots and chukkas are better bets than office-y Oxfords. But some examples can be very smart, some very casual. So tread carefully.

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Get Your Kicks

Many smart casual guides rule trainers out completely, but that’s a little old-fashioned.

Where trainers are permitted, the recommendation is typically a classic style such as Converse Jack Purcells, Adidas Stan Smiths or Common Projects in white, and that’s not wrong. But a more formal dark colour is smarter in more ways than one: they’ll be less likely to draw the eye, and therefore disapproving glances, or show dirt.

In terms of fabrics, shiny, smooth leather is smarter than matte, coarse canvas, and suede is somewhere in the middle. Knitted trainers can also look smart if they’re dark, but they’re maybe a tad too modern for some circumstances – and a step too far from proper shoes.

Leather sandals? Sometimes. Flip flops? Never.

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Common Smart Casual Dos & Don’ts

Do: Cover Your Bases

If you wear shoes that aren’t trainers and trousers that aren’t jeans, you’ll sidestep most smart casual pitfalls. A blazer will make you practically bulletproof.

Don’t: Uncover Your Arms

Whether they’re attached to a shirt, polo or T-shirt, short sleeves are casual (actual shorts even more so). Check that it’s safe before unholstering the guns.

Do: Lose The Tie

Outside of work, smart casual almost never calls for wearing a tie. A grandad shirt, polo, or roll neck will remove any ambiguity, or the impression that you forgot your neckwear.

Don’t: Forget The Tie

Disclaimer: if you’re not sure, and it’s a formal smart casual occasion, or a job interview at a casually dressed company, then you’ll never regret carrying a tie.

Do: Get Your Coat

Performing the same elevating effect, a neatly cut overcoat can even take the place of a blazer for informal smart casual events where you’ll take it off anyway.

Don’t: Stitch Yourself Up

For formal smart casual events, you might want to keep your blazer on, so wearing a removable overcoat over the top might be better than a knit underneath.

Do: Pattern Up Properly

With the exception of corporate pinstripes, patterns make pieces such as blazers and shirts look more casual, and you look less like you came from the office.

Don’t: Try And Be A Legend

T-shirts are already casual, so avoid patterns, logos, slogans or (shudder) jokes. “Liquor in front, poker in rear” only advertises that you’ve got nothing upstairs.

Do: Keep It Tight

As outlined above, silhouette also determines formality. So ensuring that casual pieces fit correctly is one way to convey smartness. We said ‘casual’, not ‘sloppy’.

Don’t: Cut Off The Supply

There’s a difference between ‘fitted’ and ‘clingfilm’. Smart casual clothes that are too tight make you look like you’re gussied up for a night at some tacky nightclub.

Do: Get A Sweat On

A hoodie? Irredeemably informal. A blazer in the same material? You got game. A plain sweatshirt can also substitute for a knit under a casual tailored jacket.

Don’t: Jog On

Trousers or chinos with sporty drawstrings or cuffs are one thing, but jersey sweatpants are just barely permissible as casualwear. Remember: it’s smart casual.

Do: Roll With It

Smart casual is also about how you wear it. Take the formal edge off by rolling up your sleeves and the hems of your chinos to expose a touch of mankle.

Don’t: Let It All Hang Out

If your shirt is poking out from under a casual jacket like a bomber, that’s one (tolerable) thing. But if it’s protruding from under a blazer? Get tucking.

Do: Give It A Little Extra

Switch your leather dress watch for a sports one with metal bracelet or Nato strap, and your leather belt for a woven one, maybe in a colour other than brown.

Don’t: Sock It To ‘Em

More than one online ‘style’ guide proposes expressing your personality through the medium of coloured or patterned hosiery. Don’t do this. Really, don’t.

5 Key Smart Casual Pieces

Unstructured Blazer

How many times can we advocate a blazer? At least one more. There’s no way around the fact that the quickest way to nail smart casual is by throwing on a tailored jacket, which is also a workhorse of business casual. So get you a blazer that can do both, ideally.

For it to fly as smart casual, the blazer should be made from a more textured fabric than an average suit jacket, cut slightly shorter and constructed less rigidly. This also makes the process of throwing it on a whole lot easier.

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‘Blazer Bomber’

Yes, a blazer is the alpha and omega of both business and formal smart casual. But what about the occasions when a tailored jacket, however unstructured, is too smart? Enter the ‘blazer bomber’.

The style comes from the uniform-wearing armed forces, so packs a certain formality payload. But for it to pass inspection as smart casual, the bomber jacket should be slimmer than a military-issue MA-1, in a dark colour (such as navy or black) and made of a more luxurious and less lustrous fabric than the standard shiny nylon (preferably wool or cotton). For informal smart casual missions, this is your wingman.

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Chambray Shirt

Oxford button-down shirts are equally at home in business casual as they are smart. Except that they’d be at the office, of course – unless you work from home, in which case you probably won’t get dressed at all. So, in the interests of variety, our smart casual endorsement is the chambray shirt.

Even though it’s not the same as denim (which is woven in a twill rather than alternating warp and weft), chambray looks similar and can come in a variety of weights and finishes. Generally, though, it’ll casualise a smart outfit or smarten a casual one – but not too much either way.

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Dark Jeans

Like the polo shirt, chinos or ‘khakis’ (technically a colour, not a style) are one of the building blocks of business casual, and can be extended into smart casual.

Given that the latter is more casual than the former, and we don’t want to repeat ourselves any more than is strictly necessary, we’ll plump here for plain, dark selvedge jeans with minimal bells, whistles and western pocket detail.

You don’t have to go indigo, though: black jeans can look just as smart, if not smarter.

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You don’t need us to nominate trainers, and you probably own a viable pair. A more useful addition to your smart casual arsenal is a pair of shoes that don’t make you feel like you’re going on a night out to a bad club.

Brogues are a smart casual standby, if a trifle fogeyish; Chelsea boots can strike a more rock ‘n’ roll note. But we’re making a case for Derbies.

They’re slightly more fashionable than wingtips, as evinced by hip brands like A.P.C. and Ami, which have started producing them, while the chunky soles imbue them with a hint of parade ground or even punk kick-assery.

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