Smart Casual – Two Contradictory Thoughts

Is any dress code likely to strike as much fear into even the most sartorially self-confident of men as smart casual? Reading that horribly nebulous phrase on an invitation is to enter a whole world of confusion. Following George Orwell’s ‘doublethink’ – the ability to hold two contradictory thoughts in one’s mind at the same time – to be smart and to be casual simultaneously does not sit comfortably.

It would be much simpler for all concerned if those suggesting this dress – something of a panicky cop-out on their part, implying as it does that you should dress up but not too much, be comfortable, but not entirely – reverted to that which was once clearly understood: the distinction between formal dress and, well, everything else.

Featured image (top) courtesy of Brunello Cucinelli.

Formal Smart Casual and Informal Smart Casual

“Just because an event is informal it is not synonymous with making no effort.”

Boglioli Blue Slim-Fit Wool-Hopsack Blazer, £520 at MR PORTER
Brunello Cucinelli White Button Down Shirt, £290 at BRUNELLO CUCINELLI
Suitsupply Grey Trousers, £129 at SUITSUPPLY
Crockett & Jones Dark Brown Pebble Grain Loafers, £525 at CROCKETT & JONES

Indeed, consult the historic etiquette guide Debrett’s – apparently for people who still dress differently depending on whether they’re in the town or the country – and it cuts the cake in even finer slices: smart casual becomes ‘formal smart casual’ (above) and ‘informal smart casual’ (below). The former requires the wearing of a good quality jacket or blazer, trousers other than jeans, a shirt with a collar, and shoes that are not sneakers or sandals. Ties are not required.

Boglioli Sand Basketweave Linen And Cotton-Blend Blazer, £590 at MR PORTER
Sunspel Rack Stitch Polo in Off White, £175 at SUNSPEL
ARKET Slim Cotton Stretch Jeans in Dark Blue, £55 at ARKET
Velasca Urtulan Brown Suede Derby Shoes, £204 at VELASCA

The latter, ‘informal smart casual’, allows jeans back into the fold – as long as they’re clean, dark and un-distressed – and throws in the option of wearing a polo shirt rather than a traditionally collared shirt. “Just because an event is informal it is not synonymous with making no effort,” as Debrett’s has it. Think of it as conventional clothing of the kind you’d wear to meet your prospective mother-in-law for the first time. It’s been considered, but you’re not dressed as though you’re actually about to get married.

Corneliani, with the addition of a suede bomber beneath a blazer. Not for everyone but it works in similar shades


If this sounds familiar, that is because ‘informal smart casual’ as defined above is rather the norm these days. As it happens, men’s style has shifted as if to accommodate smart casual, as formality and ‘casuality’, so to speak, have become increasingly blurred. The Beat poet Jack Kerouac once noted that he felt required by the norms of his time to wear blazer and tie for official publicity stills, though in his personal life dressed much more at ease in sportswear and military surplus. This was a time when perceptions of hip – to use the terminology of Kerouac’s circle, as it defined this new, creative lifestyle of the loose and easy – were beginning to be formed on the street and filter up, not trickle down from further up the typically formally-attired social ladder.

A New Dynamic

Ermenegildo Zegna

Casual, but still smart-casual from Ermenegildo Zegna

But casualwear today, in fact, represents a new dynamic – that of a hybrid style that perfectly suits smart casual. This shift has meant that casual is now defined more by the details in men’s clothing than by the obvious visual cues and stereotypes of the past. Casual clothes fit well, they don’t hang off the body. The silhouettes that perhaps distinguished formal attire are no longer owned by it. Casual clothes still hold a clean line, but do so without the use of stuffing. Shirt collars are more likely to have an unlined collar, a jacket be unlined and unconstructed, while a tie – worn because one wants to, not because one has to – might be slim and knitted, rather than fat and glossy.

Officially each garment fits easily within the pantheon of smart casual; but each is now easier to wear.


Of course, there remain out-and-out exclusions. Forget those garments typically worn for extremes of weather, so your Hawaiian shirt and flip-flops are out. But then no man should wear flip-flops, ever, anywhere. Forget too those created for specialist use, even if this is just historically-speaking – so best leave the original Adidas Sambas at home, no matter how collectable they are. And take a break from your combat pants, even the slimline ones (and, while you’re here, why are there slimline combat pants in your wardrobe?).

Specialist even includes what you might wear if – use your imagination here – you were, say, CEO of a multinational presenting an annual report to shareholders. Too formal, too crisp, too shiny, too proper – it’s all out.

A more casual approach from Chester Barrie, but with a smart edge

Five Golden Rules of Smart Casual

But there is little about the rest of what a man might reasonably wear to meet the smart casual diktat that could really be considered to mark anyone out as less than respectable, as it once might have just a few generations ago. And ultimately that’s all smart casual dressing is about: looking respectable.

Of course, respectability is in itself a rather dated concept, at least when it comes to clothing, so here are five golden rules for those seeking to be better safe than sorry.

  1. Since denim is still, even today, loaded with class associations for some people, just don’t wear it unless it’s exceptionally smart.
  2. Since tailoring is, remarkably, still associated with being ‘properly’ dressed, just wear a jacket.
  3. When in doubt, stick to darker shades.
  4. Wear the best version you have of whatever that garment is and in an appropriate material for the season (think linen and cotton in summer; flannel and wools in winter).
  5. Whatever you end up wearing, wear that garment in its best condition, too: make sure it’s clean, pressed and polished accordingly. Tuck it in. Button it up. It’s a matter of opinion – and that’s the problem – but everything else goes.

Oliver Peoples Boudreau L.A

Why not team your smart casual attire with a pair of Oliver Peoples Boudreau L.A Sunglasses, £206 at PRETAVOIR


Indeed, whereas smart casual might once have perplexed, now it’s as good a definition as any as to how most clothes-conscious men dress outside of work (and, increasingly, in it with the rise of business casual dress codes) much of the time. Which is why it’s probably a term that’s set to face extinction, most likely after a spell of righteous ridicule as being as terribly of its time. The first recorded use of ‘smart casual’, a phrase more closely associated with the 1980s, actually dates to 1924, in a reference to women’s dress in Iowa’s ‘Davenport Democrat and Leader’. One could well place a bet that one century on, come 2024, ‘smart casual’ will sound just as quaint as the name of that newspaper.