How do you define ‘cocktail attire’? Like many of the puzzling dress codes that crop up on fancy invitations now and again, the barometers are not immediately clear – at least, that is, for men. This is one of the (very) few occasions in life when women have it easier. There’s even a book on the topic by fashion writer Laird Borrelli-Persson aptly called The Cocktail Dress, which discusses in detail the dress that inspired the code.

There is no such thing for men, however. ‘Cocktail attire’ implies formality but just how smart should you go? The murky world of tailoring comes laden with its own rules and regulations – which should you comply to and which can you ignore completely?

What’s certain is that cocktail dress is occasion-wear; it’s reserved for special events and one-off evenings that require something a little different – it’s certainly not your 9-5 business suit. But it’s not black tie, either. What we’re really talking about is a good excuse to dress up, to push the boat out; so whichever way you chose to tackle it, take a cue from the fairer sex and have some fun with what you wear.

The History Of Cocktail Attire

If you were wealthy and leisurely enough during the 1920s and 1930s, there was a chance you spent a ‘cocktail hour’ or three between lunch and evening enjoying plentiful alcohol. It was the lubricant for a new kind of social gathering – and since social events were then also defined by the appropriate clothing, ‘cocktail attire’ came into fashion. Then it was a notably formal look.

It took a more relaxed, vibrant, post-war, American version of the cocktail party to admit to what the drinking of cocktails normally did: loosen everything up. And so too with men’s dress: enter jackets in fancy silk brocades. It’s essentially to this mode of dressing that cocktail attire today takes its inspiration – at the more dandy end of semi-formal style.

In the decades since, the dress code has taken cues from the styles of the day, but the intention has remained the same. It’s an excuse to dress up and show off.

What Cocktail Attire Means Today

‘Cocktail attire’ is a dress code that’s increasingly likely to appear at the bottom of an invitation – but, like ‘smart casual’, has no set definition. For some it’s still dress for a largely formal, officious event akin to a business launch. But, more typically, it’s an invitation to dress up, and decidedly not in the way one might for a court appearance.

Rather, this is dress for the party, soiree, evening drinks as a prelude to an expensive dinner or perhaps an anniversary, Valentine’s Day or wedding bash. Typically it’s something of a big celebration. “That makes the clothing you wear on the cusp of eveningwear but more colourful, a freer style but a bit flashy,” as the tailor Mark Powell puts it. “It’s dressing for what should be a fun event.”

“It’s all about being elegant and slightly louche with it,” argues designer Oliver Spencer, whose Favourbrook brand is focused on cocktail attire. Once cocktail attire might have meant respecting more rigid rules. “Now dressing up in this instance probably does still mean a smart jacket and trousers, but you can dispense with the tie, because you’re definitely not at work. Cocktail dress is an opportunity to dress in a way that’s relaxed but super-luxe. It’s about looking your finest, in some finery.”

Cocktail Attire Style Tips

Think About Fabrics

Flat, woven clothes that work for the kind of clothing worn in a more conservative environment might be traditionally smart, but aren’t necessarily suitable for a cocktail event.

Instead consider cloths of interest, with a distinctive texture or sheen – the likes of velvet or silk – and patterns that might look out of place in many working environments – windowpane checks, for example. Glen checks, herringbone and sharkskin also work well.

Casual Is Good – To A Point

Cocktail dressing is about being precise but not stiff. “But, when it comes to cocktail attire, there is still definitely ‘too casual’,” argues Spencer. “You could wear a T-shirt, for example, but only under a smart jacket. Sneakers are out, no matter how jazzy they are.” Denim is typically frowned upon too.

Consider Colour

Colour is a major consideration, “because colour can go very wrong,” says Powell, “and if you’re unsure it’s better to accessorise with colour rather than wear it in the clothing.” He opts for pinks and turquoises in accessories – in which you can go bolder – but deeper richer shades of purple and green for jackets.

When in doubt, midnight blue mohair is a great go-to choice: it’s flattering to most complexions, photographs well, and looks good under bright lights. “Wear it with a beautiful white shirt and black loafers,” advises Nick Hart, founder of red carpet go-to brand Spencer Hart. “To wear cocktail attire in an incredibly pared-down way works just as well.”

Keep It Clean (Literally)

Clothes need to look fresh on, be properly ironed, neatly folded and polished, as is appropriate. There’s no excuse for looking slovenly – you are, after all, attending a special occasion.

Heed The Invitation

Although ‘cocktail attire’ may be what’s prescribed, always be mindful to read between the lines and note what the event is actually for and who will be present. “If, actually, it really is a work event and you need to impress your boss, you may still need to conform more than normal,” says Hart. “Then again, cocktail attire can be a chance to experiment.”

Keep In Mind The Time Of Year

The summer allows for the wearing of lighter colours and fabrics, such as linen (which also keep you cooler, of course). For the colder months, richer shades and layering may feel more fitting. Likewise, is it a daytime or evening cocktail event? The later it is, the more rakish your attire can be.

Details Are All-Important

Even if you’re forced to wear the same suit you wore to work, a few key details – the right scarf, a certain choice of sock, a boutonniere – can be enough that you don’t feel entirely out of place.

Key Cocktail Attire Pieces & How To Wear Them

The ‘Suit’

Separates – smart jacket and smart trousers – typically work better than a standard suit. This allows the wearing of more sober, pressed trousers and, off-setting this, an unusually flamboyant jacket or blazer. This might be in an atypical finish or shade – olive green or burgundy rather than grey.

This kind of blazer may also “have the kind of detailing not typically found on a more conventional suit jacket, the likes of a silk grosgrain shawl collar, turn-back cuffs or a low, single button fastening,” says Powell. If you choose to wear a suit, select one you wouldn’t wear to the office, either for its colour or cloth.

The Shirt

Like the jacket, a cocktail event gives license to wear a more glamorous style of shirt – with a more distinctive collar shape or cut of cuff. Dress shirts are not easy to pull off, however, and – Powell warns – should only be worn with an appropriately restrained jacket. Don’t wear both at the same time unless Austin Powers is your style hero.

If a more standard shirt is being worn, make sure it is white or in a block colour and the kind to hold a crisp, stand-up collar: a point collar, rather than spread, works well. If choosing to wear a tie with a more sober shirt, choose one with a point of interest, for its colour or pattern.

The Shoes

The definitive cocktail event shoe of choice is the loafer – tasselled, suede or penny. A loafer that verges on the house shoe/slipper is a stylish choice: “It’s the kind of shoe you might only change into when you get to the event, but I doubt many men would do that,” says Spencer. “Certainly what you don’t want to do is turn up in a pair of brogues. No ‘country’ style should be seen at a cocktail event.”

Leather-soled Oxfords and monk strap shoes are also acceptable choices, especially when polished to a bright shine.

The Roll Neck

The perfect alternative to wearing a shirt, the roll neck still frames the face but is inherently more relaxed, and doesn’t – unlike an open-neck shirt – sometimes look lost without a tie. Spencer recommends opting for one in cotton, silk or merino rather than traditional heavier wools. “Otherwise you’re going to end up looking rather sweaty at your event,” he warns.

The Accessories

The cocktail event is the definitive opportunity to accessorise in a way that would look too flamboyant in a work scenario. “[It’s] a chance for some self-expression,” says Spencer. He suggests wearing a pin on your jacket’s lapel, using a pocket square or adding a touch of colour and pattern in the form of a silk neck scarf – he favours polka dots.

Distinctive cufflinks or a statement watch are the acceptable face of male jewellery at a cocktail event.

Common Cocktail Attire Dos & Don’ts

Do…

Respect the dress code. ‘Black tie’ is simple. ‘Business attire’ is easy. We all know what they mean. ‘Cocktail attire’ is fuzzier but still needs to be respected if that is what has been asked of you. Don’t just wear what you like because the lines aren’t crystal clear.

“Go into a cocktail event with the right attitude,” says Spencer. “Your outlook needs to be as expressive as your outfit. Go in thinking you’re going to speak to everyone there.”

Dress within your comfort zone. “If you’re not happy wearing something you wouldn’t normally wear, don’t – because you won’t wear it well,” says Powell. It’s by no means a disaster to wear a well-tailored mid- through to dark-grey (though not black) suit, crisp shirt and understated tie to a cocktail event.

Order the perfect cocktail to accessorise a fashionable outfit has to be suitably fashionable too: the simplicity and drinkability of a Negroni always works, or, to look more sophisticated, request a boulevardier – it’s a Negroni made with bourbon rather than gin.

Think red carpet. The style of dressing for men on the red carpet now – seeking more of the attention traditionally reserved for the women – is increasingly close to that of cocktail attire, argues Powell. “There’s more of a crossover because both are aiming to make a statement, without crossing the line into fancy dress,” he says.

Don’t…

Overdo it. Yes, a cocktail event is a rare occasion when a man might dress in an uncharacteristically ornate, even baroque way. But you can still end up looking like a Christmas tree. Be flashy – but in small doses, not all over. “Just be subtle with it. Don’t be garish,” says Powell.

Ask a stranger what they do for a living. In the art of making small talk – which is what cocktail events are for, not for dancing on the tables – nobody wants to talk about, or be defined by, their work. Ask instead, perhaps, what they do for fun.

Confuse cocktail attire with black tie or dinner dress, even though you may well be dressing for dinner. Black tie is too formal: it’s about following very strict rules. Cocktail attire is less formal: it’s about breaking the rules of formality by looking like an individual.

Attempt to out-dress others, especially if there’s a guest of honour. Likewise be mindful of the tenor of the event; and, if you really not sure, there is no harm in asking – the host’s idea of ‘cocktail attire’ may be more formal than yours. Better to ask than turn up and be forever remembered as ‘the guy in the red jacket’.

Overstay. Always leave before the cocktail party is over, with your dress in the same state of elegance as when you arrived. Cocktail events are in part about peacockery – and about maintaining a certain poise and self-control throughout.