Why ‘How do I look?’ is one of the hardest questions to answer

Continuing her series tackling socially unacceptable questions, Christine Manby asks if it's ever OK to ask someone how you look

(Tom Ford)

It’s Saturday night. You’re going out. You’ve been looking forward to this all week. You’ve got your glad-rags on. Your hair’s gone right. You blow a kiss to your reflection in the bathroom mirror and your reflection blows a kiss right back at you. You’re ready to go.

“Taxi will be here in 10 minutes,” you tell your loved one / flatmate / party partner for the evening.

“Nearly ready,” they assure you. You sit at the bottom of the stairs for the next five minutes, watching the little car icon on the cab app draw closer.

“Cab’s by the roundabout now!”

Four minutes to go. The cab’s just three streets away.

“Another minute!” comes a cry from the bathroom.

“Don’t forget they charge waiting time!” You try to hurry things along.

With two minutes to go, your party compadre finally appears and stands in front of you, wearing what looks like a butcher’s apron (clean) over a pair of lederhosen (possibly not clean).

“Ta-daa!”

They give a quick twirl and smile at you hopefully before asking one of the most difficult questions known to humankind.

“How do I look?”

Oh hell. The pin is out of the grenade.

(Tom Ford)

Of course, if you’re going to the sort of party where a butcher’s apron over a pair of lederhosen is actually quite a low-key interpretation of the dress code, you’re in the clear.

“Perfect, darling! Here’s the car. Let’s go.”

But if you’re on your way to your grandmother’s eightieth, your godson’s eighteenth, or any other kind of social occasion where even wearing a perfectly normal leather jacket raises eyebrows and encourages mutterings of “up for a bit of bondage, are we”, then you are in trouble. Your sixty-something cousin Jerry is going to see those lederhosen and throw his keys straight into the fruit bowl. If only your beloved had put on those nice black trousers they usually wear.

“Well?” They press for an answer.

You could try saying it in body language.

“You look, ah, you look…’ followed by a Gallic shrug combined with the Italian hand sign for “I will kill your personal shopper”.

Or you could try suggesting a small outfit tweak.

“Maybe with a cashmere sweater on top?”

“It’s 30 degrees Celsius out.”

Or you could try being honest.

“I prefer you in that other thing.”

“What other thing?”

“Anything. Anything at all.”

Whatever you do, if you hesitate to respond, all is lost. Everyone knows that hesitation in answering this particular question really means, “You look like you just escaped naked from a serial killer’s cellar and grabbed a random selection of his clothes on your way out.”

Yet if you’re not open about what you think when someone asks you how they look, aren’t you doing the other person a disservice? You may be wary of hurting their feelings but if you know they’re not looking their best, or are actively looking like a hot mess, aren’t you setting them up to be even more hurt by not saying so before someone else does? Don’t we ask questions in the hope of receiving an honest answer? Well, of course we’d all like to think we do. In reality, what we’re usually after is the real-life equivalent of an Instagram “like” for our banana yellow flares.

(Tom Ford)

My personal feeling is that if someone’s dress is tucked in their knickers, you should tell them. Likewise, if their too-tight trousers have split up the back and their undies are on show, you really ought to let them know. But if someone asks you how they look and you can’t see their nipples and you’re pretty sure that no-one will be harmed in the wearing of that outfit, then what the hell?

“Darling, you look amazing” is always technically the truth, if you go by the Oxford Dictionary definition of amazing as “causing great surprise or wonder”. Shock and awe in sequinned designer chaps.

Talking of “shock and awe”, perhaps it was fear of hurting Melania’s feelings, by telling her she looked flat out wrong for the occasion, that led to her latest wardrobe mishap. She headed out on an official visit to children separated from their parents at the US border wearing a Zara parka bearing the legend “I really don’t care, do you?” It was a strange sartorial choice to say the least. Why didn’t anybody question it before Melania stepped into the public gaze? The White House staff may not have wanted to upset the boss’s wife. Instead, people were upset all over the thinking world.

Melania’s parka reminded us that while we all like to trot out the old adage that appearances don’t matter, the clothes we choose to wear do send out messages. Not usually a literal message, as in the case of Melania’s parka (which her husband quickly defended as being two fingers to the purveyors of fake news), but important messages none the less.

There is a growing industry dedicated to deciphering Melania’s outfits. There were those insanely high white heels she wore when boarding Air Force One en route to visit people made homeless by the storms in the Gulf of Mexico in September 2017. A month later, she wore a see-through top to celebrate Hispanic Heritage Month.

What was Melania thinking when she chose each of these outfits? Did she not ask anybody “How do I look?” before stepping out in glamour model chic that was bound to distract from the gravity of the occasion?

In contrast, there have been moments when Melania has dressed like an extra from The Handmaid’s Tale. The scarlet Alice Roi coat she wore in March 2017 was pure Offred. The voluminous dark burgundy coat-dress she wore on the Trump’s visit to South Korea would have been suitable for a commander’s wife (if it came in green). It was an outfit at the opposite end of the style spectrum from the figure-skimming look her husband typically prefers. The enormous sleeves of the Roksanda dresses Melania sometimes favours are a neat way of preserving personal space if you don’t want anyone touching you with their tiny hands.

Are Melania’s wardrobe choices really unthinking or is she actually more like Phyllis Latour Doyle, a British secret agent in the Second World War who sent coded messages in her knitting. Having parachuted into occupied Normandy, Phyllis used her cover that she was an innocent handicraft-crazy local to get friendly with German soldiers. When she heard something important, she went straight to her knitting basket and knotted the information into silk threads using Morse Code. She disguised the silk threads as hair ribbons. In Belgium too, the Resistance sent messages about enemy troop movements knitted into jumpers and scarves.

Maybe Melania’s Serena Joy style is a nod to observers that she gets it. Maybe the unfortunate parka was actually two fingers to her husband. Maybe even that see-through top Melania wore as she stood behind Trump at the Hispanic Heritage Month event hid a coded message. “Would you look at this tit?”

“But how do I look?” Going back to your dear friend, dressed for the Ruby Wedding celebrations in a butcher’s apron and the lederhosen. Maybe the way to answer their question is to first ask, “What exactly do you want your outfit to say?”

Christine Manby has written numerous novels including ‘The Worst Case Scenario Cookery Club’