Former British Vogue editor Alexandra Shulman photographed working at home in her garden
Former British Vogue editor Alexandra Shulman photographed working at home in her garden © Howard Sooley

When it comes to the “out-of-office” dress code, there are two main camps. There are those who make an effort, heeding Diana Vreeland’s advice that “you gotta have style. It helps you get down the stairs. It helps you get up in the morning. It’s a way of life. Without it, you’re nobody.” And there are those who don’t, who follow the example set by John Cheever, who admitted that “a great many of my stories were written in boxer shorts”. In his early career, the American author would put on the only suit he could afford, head to a windowless basement room, hang up the suit, and then write until nightfall.

Whether it’s boxers or Berluti, what the “Skype set” wear to work is increasingly relevant. The number of self-employed people in the UK increased from 3.3m in 2001 to 4.8m in 2017. Remote working is on the rise, boosted by new technology such as group messaging and collaboration “hub” Slack, and set to be facilitated further by 5G. Then there’s the boom in co-working spaces, shared offices where one must work hard to strike the right nonchalant note.

Emma Gannon, author of The Multi-Hyphen Method: Work Less, Create More, and Design a Career that Works for You, insists on some formality in one’s home-office wardrobe. “We need to get rid of the stigma that working from home is just people sat at home putting a load of washing on and stroking the cat,” she says. “It’s important to take yourself seriously. Get dressed and put on something nice! It doesn’t matter if you’re the only one who is going to see it, it can totally transform your motivation levels.” Domestic guru Marie Kondo also counsels against the habit of demoting outdated clothes to “loungewear”, warning that “what you wear in the house does impact on your self-image”.

My freelance friends are divided in their attitudes to working-from-home style. Melissa Katsoulis, author of Telling Tales: A History of Literary Hoaxes, says she is “very, very slobby, it’s the best thing about working from home”. She favours “old cotton leggings, baggy vests, my husband’s shirts . . . maternity clothes, basically, even though I’m not pregnant.” She adds: “If I were uncomfortable, I’d be distracted. I’ve honed my wardrobe to become ever more weird and disgusting and I love it.”

Emma Gannon
Author Emma Gannon © Harry Borden

For the novelist Joshua Ferris, practicality is the main factor in how he dresses to write at home, unlike in previous jobs. “I once worked at a funeral parlour,” says the author of The Dinner Party. “Talk about formal! There, my expression mattered, as did my haircut. I worked at an ice-cream parlour called Cock Robin where we had to wear our Cock Robin uniforms. I also worked at the mall, where I solicited public opinion on a variety of topics. There, my ties and shoes mattered . . . Now, all that matters is if I’m too cold or too hot. I much prefer things like that — elemental.”

At the other extreme is James, a forty-something wine dealer who gets up, irons a shirt, and sits at his desk in crisp chinos and car shoes. He may not have a dress code to adhere to, but clothes are still a motivational and psychological tool. Lindsay, who works in recruitment, favours pristine pilates clothes because they are comfortable and sleek, and incentivise her to work quickly because she feels as if she has an exercise class scheduled later in the day. (She doesn’t necessarily have a class at all.) James Terry, the twenty-something chief executive and founder of Study Rocket, which produces learning software to stop procrastination, also uses a sartorial “productivity hack”. When he used to work from home he would put his shoes on at his desk, despite being indoors, which he says tricked his mind into focusing.

What’s it like going from one of the most high-profile jobs in the fashion industry, with a pressure to look on point at all times, to the liberation of being seen only by the DPD delivery driver? Former British Vogue editor Alexandra Shulman, who stepped down in 2017, says: “When I was at Vogue, I would dress with a degree of formality that I don’t need for sitting at my desk or, at the moment, more likely at the table in the garden. In my Vogue life I would have to take into account what other people would assume about me from how I dressed, but when I am writing at home with the cat, that is unnecessary.”

Shulman’s wardrobe is chic and considered, but low-key. “I have a fatal weakness for quite pricey clothes that don’t look as if they cost much at all, so I am most likely to be in something from James Perse, American Vintage, YMC or a number of small labels,” she says. “I usually start the day in the dressing gown I bought a few years ago in Paris — a collaboration between the French cotton brand Simrane and the Indian Anokhi. If I am on a deadline — even a self-imposed one — I will skip that state and get into clothes immediately, probably some trousers and a T-shirt by Velvet.”

She also relishes those less frequent opportunities to dress up. “One of the joys of no longer being in full-time employment is that it is more fun for me to get togged up in the evening.”

Novelist Joshua Ferris
Novelist Joshua Ferris

What about those who work from cafés, or at one of the fast-proliferating co-working spaces? Few have the confidence to wear their old tracksuits here. Rose Cartwright, 32, a writer and creative director whose book Pure is being made into a Channel 4 drama, found that her working attire changed dramatically when she stopped writing at home and joined Second Home, a workspace with branches in London, Lisbon and — imminently — Hollywood. At the Spitalfields office, filled with mismatched mid-century desk lamps and plentiful plants, the walls are Perspex, so everyone is always on display. “A space like this is a hybrid between work and play,” she explains. “And that’s reflected in how people dress. There are so many people working for themselves and creating their own identity rather than having it meted out to them. People make an effort because they really care.”

Cartwright, who used to write in an “old sloppy Lacoste jumper and men’s jogging bottoms”, says that “deciding what to wear brings purpose and intention to my day”, combined with “a routine that simplifies the decision-making process”. She has several pairs of white Reebok Classics and Nike high-tops, which she pairs with high-waisted, cropped jeans by Cos or & Other Stories, T-shirts by Comme des Garçons Play, and a bomber jacket. She accessorises with red lipstick, gold hoop earrings and a palm tree pendant. Occasionally she will wear a fitted dress with trainers and a slouchy shirt, switching up to a loose trouser suit for meetings.

Study Rocket’s James Terry, who now also works at Second Home, rarely smartens up his usual desert boots, Levis and T-shirts, even for Skype calls with possible investors. “The kind of investors we work with know the tech community are pretty informal,” he says. “If they cared about how I dress, maybe I wouldn’t really want to work with them.” Yet he does concede that a meeting with a private equity fund at, say, London hotel The Ned, might necessitate a more classic look.

Artist Luke Hall
Artist Luke Hall

The artist Luke Hall also works in a shared studio and recently bought what he calls “a kind of ‘work suit’ — a canvas jacket and pair of trousers in tan cotton from utilitarian English brand Old Town. Like Jackson Pollock and Picasso, Hall has struck on a rugged workwear aesthetic, and he takes pleasure in the heavy cloth of the suit. “Because I am an artist/designer, I consider everything around me and in my studio . . . so of course what I wear, even to make a mess, is still considered,” he says. “Also I like having clothes for individual tasks/situations — for example, loose silk pyjama shirts for summer holidays or tartan pyjamas for Sunday mornings. I think it’s good to have outfits for particular scenarios because they help you to get the most out of them, somehow.”

Perhaps the out-of-office wardrobe is not about opting out of a formal dress code, but forging your own little sartorial fiefdom. The new way of working has offered us a chance to experiment with new looks — and take pleasure in the freedom.

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