Larry David looks cool. As much was pointed out in a piece we ran last week in which the smart-casual clothes of the Curb Your Enthusiasm creator and star were picked over and celebrated. He was hailed as an “accidental style icon”.

From the blazers to the Ecco shoes, the understated outfits read just as David reads. “None of it screams stylishness or a great interest in current trends, more just a man who knows what he likes and is comfortable wearing it,” Larry Ryan pointed out.

This idea, of being accidentally stylish, comes up time and time again. Joe Biden has more than once recently stepped out wearing trainers by California-based Hoka, alongside his navy blue suit. The look has been written up as being “accidentally cool” in a gorpcore vein and it has been said that he “appears to have been taking his cue from the catwalks of Milan and Paris”. Princess Anne wearing retro suiting, a Longchamp Le Pliage travel bag and her beloved Adidas wraparound sunglasses to touchdown on a recent trip to Sri Lanka was also noted as having that very same quality.

There are plenty more examples: David Hockney, who for some is a style icon of the expected ilk, also sometimes gets labelled as accidentally cool in his yellow Crocs and bright suits, ditto the late Iris Apfel and Mark E Smith. Joan Didion has more than once been called an accidental fashion icon – no wonder she was tapped for a Celine campaign.

It is striking that these “accidentally stylish” folk seem often to be white – the idea of failing up works even in the realm of how people read your sartorial choices.

But is there really any such thing as being accidentally stylish? David thinks deeply about his clothes. Biden chose those shoes and those suits, or at the very least agreed to put them on; ditto Princess Anne, who has been using her Longchamp bag, currently lusted after by a new generation on Depop, for years and who knows the optical importance of the moment you land on the tarmac for a royal tour. Joan Didion’s outfits were likely as considered as her prose and Hockney, well, he knows his way around a colour palette.

As an idea, being “accidentally” anything is an interesting one, particularly when it comes to something aesthetic. For its obvious limits look to the accidentally Wes Anderson phenomena, which started out as architecture and laundromats that just so happened to have something of the director’s trademark whimsical, pastel aesthetic, yet increasingly became people highly intentionally mimicking the look and feel of his films for the ‘Gram and hashtagging them “accidentally Wes Anderson”.

Often these “accidental style icons” seem to be people over 60 who have tapped into a trend it is assumed they would not wilfully tap into. The real accident here, the idea seems to say, centres on Biden not knowing the gorpcore signifiers of his kicks. Princess Anne not clocking that her suiting fits neatly with cuts that have been spotted on recent Prada catwalks. Hockney not realising the cachet of Crocs, and so on. All of which is possibly true, but is often a patronising assumption.

Perhaps this idea of accidental stylishness feels so interesting in this moment – refreshing, almost – because it is so counter to the recent dominance of looks that are an in-joke or require some expertise to fully understand them. The concept of IYKYK, or “if you know you know”, is fuelling hype around trainers, highbrow merch, whether litcore caps or A24 shirts; and the models of the moment.

It was the architecture behind the biggest sartorial mood of last year – the quietest of luxury is predicated on certain people – dare I venture, those that the wearer deems worthy of impressing – clocking that a garment is a $9,000 cashmere jumper by Loro Piana rather than a Uniqlo staple, despite no obvious logos signposting such. It is elitist where just happening to wear something is not.

The pull of these so-called accidentally stylish outfits is down to the ease and insouciance with which they are apparently pulled off. That is the nub of the thing. To not look like you have tried too hard. Inspired by Princess Anne for her latest menswear collection in Milan, designer Silvia Venturini Fendi said, tellingly, “she’s kind of an anti-fashion person and, to me, that’s something that’s actually very fashionable and chic”.

But to think all of this comes without intention is folly. There is arguably an artfulness to accidental style. There is a word in Italian: sprezzatura, which is defined as “a certain nonchalance, so as to conceal all art and make whatever one does or says appear to be without effort and almost without any thought about it”.

No judgment on those who care nothing for style or those who care everything for it, but this idea of finding what works for you and not letting the noise distract you, is aspirational. Part confidence, part dressing with half an eye on what is current but not letting it overpower what you actually want to wear. Using comfort and what makes you, you as your north star rather than what Kylie Jenner wore last week.

Perhaps that is the real reason why many of these so-called accidental style icons are of a certain age – it can take time to know who you are, and to find a style to match.

What’s hot – and what’s most definitely not – this week

Going up

Demi-wear

From JW Anderson to sustainably minded underwear brand Fruity Booty, the garments currently blurring the line between under- and outerwear are more pointelle than pointedly sexy.

The ‘bad mug’

Chipped, ugly, just not quite right. It’s time to embrace the worst mug, says Eater, and celebrate the way it adds “suspense to an otherwise-mundane daily ritual” and character to your cupboard.

Sarah Jessica Parker’s London

From the charming Timpson’s at High Street Ken to the “exquisite TfL”, SJP’s take on the capital looks tres charmant compared to the view from the top-deck of the bus.

Going down

Bottomless brunch

Wellness hen parties, intended to enrich rather than intoxicate, are apparently becoming the more peaceful way to prepare for saying ‘I do’. Blow-up penises presumably not encouraged.

Ammonites

Coperni’s new geologically dramatic $45k bag is made of meteorite that fell to earth about 55,000 years ago. Rock on?

Dull lace-ups

Fashion is currently having fun with footwear – from Erdem to Jil Sander, personality shoes are a big hit on the catwalks (less so a dog poo-strewn pavement).

Chloe Mac Donnell, deputy fashion and lifestyle editor, solves your wardrobe dilemmas

Q: I’m looking for a chic handbag under the £90 mark. Not black, something with more of a spring/summer feel - Rachel, London

A: You’re in luck. This season the high street has upped its handbag game. This crossbody bag from M&S (pictured above) comes in a lovely grassy green colour and the gold pebble shaped fastening makes it look much more spenny than its £35 price tag. Charles & Keith has a smart chalky white bag that comes with a removable strap while JW Pei’s pink shoulder bag is guaranteed to spark spring joy. It’s worth noting that most high street bags are made from plastic derived materials such as polyurethane. So before you buy new, try a secondhand site such as Vinted or eBay.

Got your own style question? Send it to [email protected].

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