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A silk pyjama set by Scandinavian brand Toteme, one of the brands that is benefiting from the rise of sleepwear as streetwear. Photo: Toteme

Bella Hadid’s boxers, Zoë Kravitz’s slip dress – sleepwear as daywear is very much in fashion. How to make pyjamas your holiday wardrobe staple

  • The silky, fancy pyjama dressing seen in classic Hollywood films such as Rear Window is seeing a resurgence – not in the bedroom, but out and about, and in bars
  • Celebrities from Zoë Kravitz to Hailey Bieber to Bella Hadid are wearing slip dresses, boxers, drawstring trousers and more. Brands have caught on to the trend
Fashion

As someone who works from home, the blurring of lines between ready-to-wear fashion and pyjamas is a triumph.

Seminal examples of pyjama dressing are not hard to find, least of all in Hollywood: there is Grace Kelly’s (albeit extremely polished and elegant) pearlescent nightgown and negligee in Rear Window; Sophia Loren’s buttery yellow set in A Countess From Hong Kong; and Audrey Hepburn’s oversized men’s shirt and eye mask à la Breakfast at Tiffany’s.

I remember falling in love with the lacy, sheer, and ruffled mid-century sleepwear in Mad Men – especially the confection-like looks worn by Alison Brie’s Trudy.

When it comes to more recent sightings, a personal favourite involves Zoë Kravitz, who was spotted on a coffee date with her then-rumoured beau Channing Tatum in 2021 in an azure washed silk slip from New York label Araks, which promptly sold out.

 
Of course, there is the famously comfortable “nap dress” by American brand Hill House, which went viral during the pandemic and fronted the cottagecore trend at its peak.
Now, the most evident – and trendy – hallmark of the trend is the humble boxer short, which has been spotted on everyone from Hailey Bieber and Bella Hadid to models on runways at Bottega Veneta and The Row.

Even if you are not on the boxer bandwagon, sleepwear as daywear is not hard to like. Comfort-aside, it is laissez-faire dressing at its peak – alongside the likes of “no make-up make-up”, few things appear more effortless than an outfit you ostensibly rolled out of bed in.

Think of the Italian term sprezzatura, which renaissance writer Baldassare Castiglione coined and defined as “a certain nonchalance, so as to conceal design and make whatever one does or says appear to be without effort and almost without thought”.

Looking effortless, as millions of make-up tutorials prove, can be a time-intensive ordeal.

Bella Hadid wears a matching shirt, bra and boxer set in Cannes in a photo the model posted on Instagram. Photo: Bella Hadid

But when it comes to taking cues from sleepwear, this does not have to be the case. A number of brands are making a case for pyjamas as holiday wardrobe staples: see the latest advertisements for looks from Comme Si, loved by cool girls, which see sun-kissed models lounging in confectionery-coloured cotton poplin boxers.

I would take a cue from the brand’s own Instagram and wear them with a cotton button-down, a pair of their Everyday Socks and leather loafers for a coffee run.

There is also Scandinavian favourite Toteme, whose drawstring striped trousers are both enviably breezy and very much on sale; also going at a discount is the label’s matching striped oversized shirt, which I would get in a larger size and wear as a beach cover-up, or tucked into more structured bottoms, like a pleated trouser or jean.

Striped boxer shorts from Comme Si’s latest campaign. Photo: Comme Si

If you are looking for something more evening-friendly, the brand’s monogrammed silk PJ sets are a polished solution.

My instinct is to avoid wearing matching full-length striped sets out of the house, so as to avoid teetering too far into bedtime territory à la Gene Kelly in An American in Paris.

Solids, for this reason, feel more doable: a friend who visited Copenhagen over the summer reported seeing a number of ever-photogenic locals donning Danish brand Tekla’s unisex pyjama co-ords.

 

As a fan of their striped full-length poplin sets, I am currently eyeing the shorts and short-sleeved silhouettes in a deep royal blue; throw on a pair of chunky sandals and a tote, and you will give the Danes a run for their money – or so my shopping-addled brain tells me.

For now, I will work with what I have got, and will be wearing my striped PJ bottoms with a jumper and velvet slippers as temperatures drop.

To come full circle, I find slip dresses to be the most timeless of the sleepwear bunch. My favourite dress I own is a black bias-cut slip by Protagonist – the label is sadly no more but their signature silk pieces are not too hard to find second-hand.
A slip dress from Silk Laundry’s latest collection. Photo: Silk Laundry

It is a no-brainer when I travel, as it takes up virtually no room in my carry-on; I wear it as is on summer evenings alongside my favourite jewellery and bring a cardigan or button-down for good measure.

For the same slinky bias-cut fit, Silk Laundry makes an array of ’90s-inspired slips in neutrals, brights and playful patterns. Their site has inspired me to wear silky trousers under my slips for a more dressed-down feel – not unlike a look from Louis Vuitton’s spring 2022 catwalk show, though I do not think I will be wearing jeans underneath in full aughts fashion just yet.

Elsewhere, Araks’ Georgette slips are now available in a range of luminous colours – including Kravitz’s sky blue – and just as flattering, and I would be remiss if I did not mention Skims’ cult favourite Soft Lounge Slip, beloved by TikTokkers and celebrities alike for its sculpting silhouette.

For high-impact party looks, look no further than Sleeper, whose feather-trimmed satin sets and slips are perfect for going straight from the function to bed in style.

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