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Home / Entertainment

Everything Succession taught us about how the super rich dress – for better or worse

By Lisa Armstrong
Daily Telegraph UK·
28 May, 2023 11:12 PM9 mins to read

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Shiv Roy: Clearly never a Colour Me Beautiful expert. Photo / Supplied

Shiv Roy: Clearly never a Colour Me Beautiful expert. Photo / Supplied

This article does not contain spoilers for the final episode.

The show, which comes to an end this weekend, took the accuracy of its characters’ wardrobes to new heights for TV.

A 2014 Vanity Fair Best-Dressed Billionaires list shows the world’s elite in suits that make their positions obvious. That list includes Leonard Lauder, of Estée Lauder fame, financier Henry Kravis and David Geffen, music honcho, in obviously expensive, gold buttoned suits, albeit some of them accompanied by “quirky” colourful trainers (Geffen). These billionaires didn’t feel any ambivalence about Dressing Rich. Surprise surprise, there weren’t many women.

A decade later, a still male-dominated but more conflicted kind of super elite has emerged. Mark Zuckerberg, Elon Musk, Jack Dorsey, Adam Neumann (founder of WeWorks) dress like scruffy college undergrads. Zuckerberg loves telling journalists about his rail of identical T-shirts. Steve Jobs made a point of always wearing black polo necks, later copied by Elizabeth Holmes, at one point the youngest self-made female billionaire on Forbes’ rich list, soon to be residing in jail.

Boring. Boring. But hilarious. This lot think they’re being inscrutable by refusing to engage with conventional signals of success – a freedom only the rich and powerful can afford. Succession, which comes to an end Monday, has had colossal fun with these two colliding old and new rich worlds.

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Widely held to be inspired by the Murdochs (although the show’s head writer, Britain’s Jesse Armstrong, recently revealed he drew on real life moments from the Maxwells’ psychodrama too), patriarch Logan Roy, founder of the Waystar Royco media behemoth, and his children wear the kind of “insider” labels today’s super-rich favour; understated tailoring from Loro Piana, Brioni, The Row and Brunello Cucinelli. New techie moguls like the creepily compelling Swede, Lucas Mattson, wear Fjallraven athleisure and garish, Jeff Bezos-like jackets.

Kendall Roy wears some beautiful streamlined Brioni suits but accessorises them with expensive baseball caps. Photo / Supplied
Kendall Roy wears some beautiful streamlined Brioni suits but accessorises them with expensive baseball caps. Photo / Supplied

This degree of accuracy was new for TV. Not so long ago, costume designers either didn’t have the budgets or the licence to present today’s power cabal the way they really look – i.e. discreetly semaphoring their status to fellow members of their club.

Occasionally the audience is given free rein to drool over the outfits (for my limited money, it’s Naomi Pierce, a minor, exceedingly old money, rich character who’s one of the few genuinely stylish women in the show with her expensively tousled blonde crop and minimalist monochrome outfits). But beautiful clothes for the sake of beauty, have never been the point of Succession. Unlike Jennifer Aniston’s The Morning Show for instance, where Aniston must be the only TV anchor in the world who wears taupe and navy Dior and Celine separates, rather than primary coloured dresses, Succession doesn’t shy from allowing its leads to look bad if it feels authentic or drives the plot.

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Their rampant insecurity is never more apparent than in the way its women – notably Shiv Roy, only daughter of Logan Roy – struggle to nail power chic. Unlike, say, Delphine Arnault, daughter of the world’s richest man, Bernard Arnault (who’s always immaculately tailored), Shiv can’t look too “fashion” or feminine. Delphine is CEO of Dior. She can look as feminine as she pleases.

Shiv is often seen in 'expensive drab shades and ill-fitting suits'. Photo / Supplied
Shiv is often seen in 'expensive drab shades and ill-fitting suits'. Photo / Supplied

Shiv, who works for a Democrat candidate when we first meet her, starts out wearing schlumpy H&M knitwear. The show isn’t snobbish about high street but this is a bad choice for Shiv. Infinitely less well-off characters (mainly employees at Waystar Royco) manage to look sleek and professional in Zara and J Crew. Kerry in particular uses colourful trouser suits, and a very, very shiny dark fringe, to stand out in the boardroom (and catch Logan’s eye).

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But money, as this show often reminds us, can’t buy style. Shiv, in her expensive drab shades and ill-fitting suits, has clearly never been near a Colour Me Beautiful expert. If she had, she’d stick to the emeralds, ivories and reds she occasionally rocks when she’s feeling comfortable in her skin. But she doesn’t have time. She’s fighting to be taken seriously in that shark tank. (Sarah Snook, the actress playing Shiv, was pregnant during filming and so, it transpired, is Shiv. Both actress and character, for professional reasons, were trying to hide it.)

Even when Shiv drops big money on Tom Ford, Alexander McQueen, Ralph Lauren and generally pulls her look together, she eschews anything overtly “fashion” (or maybe she’s just not that interested) because the potential for getting it wrong is so high. She’s a version of the few women who find themselves at the top end of FTSE index companies – the Elisabeth Murdochs, Elizabeth Holmeses and Sheryl Sandbergs.

Willa, married to the fourth Roy sibling, is another high street aficionado. That seems odd, since she’s disarmingly honest about her motives for marrying Connor – money. Maybe she’s worried Connor will spend all of his money on endless doomed attempts to become the next US president and is squirrelling her clothing allowance into a Swiss bank account. That said, her penchant for flirty, fitted dresses - not a million miles from Lauren Sanchez, fiancée of Jeff Bezos - that show her toned body is teeing her up nicely to become someone who’d model their First Lady style on Melania Trump. Marcia, Shiv’s step-mother, is a conundrum too. Mostly she’s ultra smart, in a severe Latin way. But every so often she cracks out a playful hair accessory. It all seems a bit jarring until you consider many of Jerry Hall’s outfits.

Succession’s Gerri, one of Logan’s long-standing inner circle at Roystar, is more consistently sure-footed in her wardrobe decisions than Shiv, probably because she got where she is on merit. But even Gerri, though generally sleek, tends to shop mid-level (including Emporio Armani and niche British brand The Fold which she probably spotted online) because like many female execs on big salaries, she doesn’t want to draw too much attention to her sartorial expenditure, even though her male counterparts spend thousands on their suits.

Gerri’s hair – let’s call it “minimally groomed” – is another stress point among fans. She doesn’t want to look like one of those bouffant-ed presenters on Roystar’s version of Fox TV so she often veers in the opposite, wispy extreme. The day she gave up completely, and shoved it into what’s become known as #sadscrunchie was a major plot tell. That very day she got fired.

The 'rampant insecurity' on show in Succession is clear in the way its women struggle to nail power chic. Photo / Supplied
The 'rampant insecurity' on show in Succession is clear in the way its women struggle to nail power chic. Photo / Supplied

Relatable as these slip-ups are, they can sometimes feel like the wardrobe department’s mistakes – until a real-life rich person pops up in something similar. The infamous Ted Baker dress Shiv wore to her mother Lady Caroline’s wedding in Italy initially drew opprobrium upon the brilliant Michelle Matland, Succession’s costume designer. What in God’s name was a billionaire doing in Ted?

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Then Justin Trudeau’s wife, Sophie Grégoire, arrived at King Charles’s Coronation in Ted Baker, another “uncool” high street brand, albeit in a colour that suited her and a style that may have been altered to fit her properly. Besides, Shiv isn’t cool. Maybe she bought it on a rushed trip to the UK (her mother’s British). Or perhaps she knew it was a mistake and wore it anyway, to snub her ice cold mother who, in old school style, has no qualms about dressing in fabulously elegant clothes.

With so many layers – literally – of nuance, the men’s looks are as interesting as the women’s, semaphoring their sweaty-palmed desperation. Tom Wambsgans, connected to the Roy dynasty precariously, via his rocky marriage to Shiv, is forever falling into sartorial mantraps, while sneering at others. His widely mocked trainers are too white. His dress shoes too dressy. If and when he and Shiv finally divorce, she may well cite Nike.

No wonder he punches down whenever he can, infamously roasting a “civilian” who interlopes one of Logan Roy’s gatherings at his $63 million Upper East Side apartment for the “ludicrously capacious bag” she’s carrying. It’s designer, but the wrong kind – a Burberry check from duty free – and its size denotes an owner who packs her own lunch and carries her heels to work.

The only character true to themselves is Connor Roy, the son who rejected the fight for dynastic supremacy, took a few hundred million instead and dresses in conventionally tailored, mostly impeccable threads. In contrast, Kendall Roy, the son most assume will succeed Logan’s throne, wears some beautiful streamlined Brioni suits but accessorises them with expensive baseball caps and giant Beyerdynamic headphones through which he listens to testosterone-boosting rap. He looks ridiculous. Part of Kendall wants to be liberal and self -made. But all his privilege derives from a “legacy” news organisation that’s about to anoint a fascist as the next US president. There are few more bathetic sights than Kendall at his bleak 40th bash, attended solely by liggers (the Roys don’t have real friends), in an ill judged, $7,000 metallic Gucci bomber jacket. Kendall’s tragedy is that he has occasional flashes of self knowledge when he realises what a dork he is.

Then again, none of the Roys are aesthetes. Their plush homes are bland, their $10,000 outfits often not quite right. They worship money not for the beautiful objects it can buy, but the power it confers. One character says the best thing that could happen after Logan’s death is for his collection of Picassos to be destroyed in a fire so his children can avoid paying inheritance taxes.

This is deeply satisfying to the rest of us. Look, says Succession, these billionaires don’t just have bad taste, some of them have no taste. All those rich people’s toys – the stupidly priced watches, the brash yachts – but no joy.

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