Tread carefully: Jayne Mansfield (centre) and Ray Walston in 'Kiss Them for Me' (1957)
Tread carefully: Jayne Mansfield (centre) and Ray Walston in 'Kiss Them for Me' (1957) © Snap Stills/Rex/Shutterstock

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OMG you look amazing! Stunning! Gorgeous! For any fashion influencer worth their selfies, receiving an avalanche of praise after posting a photo is essential. But, in the age of the throwaway social media compliment, what does that mean for real-life praise about one's appearance? Is enjoying them a symptom of an insidious "like" culture, or just a way to connect with people?

I started thinking about compliments when I stopped wearing my usual uniform of jeans, navy tops and navy shirt dresses, and went cold turkey on plain, dark clothes. The trigger was provided by pregnancy, not being in an office and hot weather. I've spent the last few months wearing maxi dresses in floral patterns, and shades of scarlet and cobalt. My current favourite garment is a Raquel Allegra kaftan in black and orange tie-dye that makes me feel like a Miami clairvoyant of a certain age.

I can't tell if it looks good, but I certainly get a lot more comments about what I wear. Some are explicitly favourable, others not so much. An oversized red linen dress has had a lot of "that looks cool" (as in, appropriate for a heatwave), and one reference to Mrs Claus. As someone who likes talking about clothes, I don't mind either way. I'm finally embracing the fact that wearing something striking is an entrée to a good fashion chat.

Renée Kuo, managing director of etiquette experts Debrett's, which has just brought out a new edition of Debrett's A-Z of Modern Manners, confirms that, "a compliment is a great icebreaker, whether at the office or at a social event". She adds: "a genuine compliment should make the recipient feel good about him or herself without causing self-consciousness."

In theory, a positive comment should come from the heart, but pitching them just right isn't always easy. Backhanded compliments from decades ago still sting the soul — "that's a nice bikini, for someone with a tan" — and not everyone has the flair of Tom Cruise in Jerry Maguire when he tells Renée Zellweger: "that's not a dress, that's an Audrey Hepburn movie".

Take the ambiguous: "That's so you." Does that suggest you have a strong signature style, like Jane Birkin? Or that you are a stuck-in-a-rut caricature in the sartorial mould of Charlie Chaplin or Ronald McDonald?

And what about the ex-boyfriend I ran into at fashion week who told me I must be "really secure" to come to a fashion show wearing brogues, jumper and jeans. Does it mean more when I get a compliment from another fashion editor than when my three-year-old says: "I like your dress, mum"? Either that's the purest kind of praise there is, or I've accidentally styled myself to look like Peppa Pig.

"I suppose I consider the highest compliment to be one that digs a bit deeper than the surface level of what I'm wearing," says Leandra Medine, founder of the online fashion magazine Man Repeller. The site is named for the type of clothes that men generally hate — low-crotch trousers, overalls, baggy shorts, shoulder pads — and revels in pushing the boundaries of taste. Medine's own eclectic, experimental style courts opinion and engagement. She wants the effort she puts in to her ensembles to be credited, rather than pursue praise for its own sake.

Medine regularly asks her 683,000 Instagram followers for their opinions on her outfits, and captions them with self-deprecating comments: "In Paris for the retired masseuse convention", reads a line under an image of her wearing a slightly clinical white tunic over white trousers. "I'm not sure that I dress to attract compliments, but I certainly appreciate peer recognition," she says. "Unless we're talking about my shoes. I recently launched my own label and whenever my shoes are complimented, my heart straight up sings." Does she think a man can compliment a woman's outfit without seeming creepy? "My inclination is to say absolutely," she replies. "But it's definitely a fine line."

For a case study in how not to tread that line, look to Donald Trump. On his first state visit to France, the US president was filmed looking Brigitte Macron up and down, gesturing towards her body, and saying "you're in such good physical shape. Beautiful." He then repeated the comment to Emmanuel Macron as if passing judgment on a prizewinning poodle at Crufts.

Post #MeToo, it's a textbook example of how a man can make a woman feel uncomfortable. Kuo says: "Men complimenting women on their appearance has always been precarious territory — especially in the workplace. A seemingly innocuous comment such as 'that dress looks great on you' may cause a female recipient to feel she is being ogled. It is wiser for men to steer clear of style and appearance-focused compliments toward women in the office."

As for how to offer a compliment without causing offence, Kuo has some simple rules. "One should be specific about the object of the compliment (handbag, shoes, article of clothing) but not venture into too much detail. For example, 'what a beautiful dress!' is a perfectly acceptable compliment as opposed to 'what a beautiful dress — it makes your waist look smaller' or 'what a beautiful dress — I bought one just like it in New York last year'." Likewise, the old "have you lost weight" tends to go down well with someone on a mission to get a six-pack, but it can come with the underlying suggestion that you looked like a sumo wrestler before.

And what about that other minefield for praise — cosmetic surgery? How do you acknowledge a sudden sprouting of a Tom Cruise-worthy coiffure or an unusually taut jawline? Cosmetic surgeon Dr Jonquille Chantrey reports, unsurprisingly, that "the vast majority of my patients definitely do not want anyone to notice they have had treatment. Their worst nightmare would be if someone were to point out an area of the face and query intervention." Instead she suggests observing that they look "brighter, fresher, more rested or slimmer".

However, Kuo adds that "while it may be deemed reverse sexism, the compliment sword doesn't cut both ways. When offered by a female colleague, a comment such as 'that's a lovely tie' or 'nice haircut' is less likely to be interpreted as ogling by a male recipient. That said, it might be best for women to avoid overtly body-focused compliments ('that shirt shows off your muscles so well') in the office."

Then again, as Esquire editor Alex Bilmes observes, "I think it entirely depends on the circumstances . . . My favourite compliment remains the time that a female colleague pinched my bum when we both worked at Vogue." Attempt at your own risk.

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