7 Times Poor Outfit Choices Told Us Characters Were Doomed on “Succession”

Succession Fashion Season Four

Succession season 4 starts with one of director Jesse Armstrong’s favourite plot devices: clothes and controversy around clothes. Cousin Greg, an under-the-radar, lumbering outsider with a surprisingly wily streak, arrives at Logan Roy’s birthday party with a date. She is toting a handbag and, according to Tom Wambsgans, the bag is not okay. Sure, we wouldn’t necessarily style the busy black and white Sandro dress with busy (and much imitated) Burberry check. But Tom’s main criticism isn’t the styling; it’s the size of the bag.

“It’s monstrous,” he murmurs, “it’s ludicrously capacious.” According to Tom, the bag could fit anything from “flats for the subway” to a “lunch pail.” Essentially, the possessions of a working-class or professional woman. He might pass out if he found out she had a laptop in there. The unspoken point being: she certainly doesn’t have a PA who carries her belongings for her.

Greg's dates "ludicrously capacious bag"
Greg’s date Brigitte and her “ludicrously capacious” $2890 Burberry bag. Image Credit: HBO/Binge

Stealth Wealth: Succession’s Fashion Legacy

In the Roy’s world, clothes less “maketh the man” than communicate their level of control, power, or vulnerability at any given moment. Brigitte’s Burberry bag indicates she’s out of the loop. While it may have set her back $2890 USD, the overt branding and the suggestion it may carry something so everyday as a laptop is everything the Roy family, and their blandly dressed hangers-on, are not about.

The series has become known for it, with Michelle Matland, the mastermind behind the “Succession” wardrobes, mapping characters’ moments of victory, defeat, and abject humiliation in Patek Phillip watches, $625 unbranded baseball caps, and puzzling Ted Baker dresses.  

Related: Is Kerry Logan’s Daughter? The Wildest Succession Season 4 Theories Brought to Us by Superfans

“Stealth wealth” has been coined to describe the bland, joyless, un-ID’able, garments worn by the Roy family. It’s Shiv in oversized H&M in the pilot episode, Roman’s refusing to wear a tie, and Kendell’s generic $970 USD Tom Ford hiking jacket. Wealth in “Succession” is careless, effortless, occasionally ugly, and intentionally invisible. 

Deviations from this tastefully tasteless style typically signal a character’s loss of control or outsider status. They usually result in a verbal dressing down or flag a character’s impending doom. 

With the series at its close, we celebrate Michelle Maitland’s diabolical work, rounding up Succession’s most cringe-worthy sartorial missteps and dread-inducing foreshadowings.

The Gift

It’s unsurprising that Tom jumps on Greg’s date’s bag with vicious alacrity: he’s been trained by the best in the fine art of dress code-violation humiliation. A grasping social climber from a middle-class background (shudder, his mother is a lawyer), he’s routinely humiliated by his wife and her family. We see this immediately; in season 1, episode 1, Tom dithers over purchasing a Patek Phillip watch for Logan Roy’s birthday despite Shiv’s repeated warnings that her father hates gifts.

Once selected, he makes several failed attempts to present Logan with the watch, before finally foisting it on him during a family baseball match with a heavily rehearsed joke. (“It’s incredibly accurate. Every time you look at it, it tells you how rich you are.”) Logan palms it off and it’s later “re-gifted” along with an NDA to a working-class family whose son was tormented by Roman Roy.

Greg’s On Deck

Every nepo baby has to start somewhere, and for Cousin Greg, the grandson of Logan Roy’s despised brother, that’s as the dogsbody for the previously-least respected character in the series, Tom. Pre securing his position at Waystar Royco, Greg shops at Goodwill for his first suit. He can’t find normal shoes that fit his enormous feet, so he lands on a pair of worn-looking loafers – that Tom feels would be better seen deckside.

Related: Cousin Greg Has Already Won Succession as the Only Likeable Character Left in the Room

Tom calls Greg out for his boat shoes moments after he arrives at Waystar, asking him if they’re speaking on the “poop deck of a majestic schooner.” Greg explains, “My credit card got maxed out, I’m staying in a youth hostel on $80 a day,” and that he’s packing free food into a dog-poop baggy because “my body has grown weak due to a lack of sustenance.” Tom is unmoved and demands a pair of Crockett & Jones cap-toed Oxfords ($838USD) “ASAP”.

Kendall in Anything Gucci 

Kendall with Naomi Pierce at his disastrous 40th birthday clad in head to toe Gucci
Image Credit: HBO/Binge

Kendall Roy consistently snatches defeat from the jaws of victory. He’s the most genuinely worrying person on the show, a self-destructive depressive with substance abuse issues and a powder-kegg personality. He also has a genuine longing to do good in the world and, thanks to his upbringing, a total inability to know how to do it. Unlike his siblings, Kendall enjoys and has a flair for fashion. He’s at his best in head-to-toe earthy Loro Piana, Bruno Cucinelli, or Maison Margiela t-shirts in states of varying cleanliness. 

He’s at his worst when he’s tapping into his “rap god” persona — whether that’s wearing a pair of Lanvin “dopey sneakers” to offer cash to uninterested young artists’ art collectives, a baseball jersey during his infamous “L to the OG” rap during his father’s 50th anniversary, or a distressing amount of Gucci at his disastrous 40th birthday party. We always know our boy is headed for a fall when he enters this mode, and it’s difficult to watch on multiple levels.

Tom’s Moncler Moment

Tom's Moncler-faux pas
Image Credit: HBO/Binge

“What’s that puffer vest full of? Your hopes and dreams?” quips Kendall to Tom in season 2. The family are on a chilly retreat and Tom is wearing an uber-puffy Moncler vest with, shudder, the brand logo. While Tom has stepped up a few notches since season 1, he still needs to learn that prominent branding is a no, and anything that draws attention is a bad idea. While the other characters dress in sleek, discrete Cucinelli vests, Tom can’t resist. Maitland told Ringer, “Tom doesn’t know what quality is; it’s not part of his history. Money equals quality to him.” Unfortunately, it doesn’t equal power. Fortunately, by season 3 Tom has swapped out his Moncler for an unbranded, $525 USD Paul Stuart vest. You live, you learn.

Shiv’s Ted Baker Dress 

In season 3, Shiv’s golden child status has crumbled, and she’s losing control of her dog’s body husband following a failed attempt at an open relationship. (Tom doesn’t want one. Shiv doesn’t want Tom.) She finds herself increasingly cow-towing not only to her dad, but her brothers, husband, and mother.  

Shiv’s outfits get more… left of field as she becomes increasingly anxious and angry. Her suits don’t quite fit; her dresses are colourful — a violation of the strict Roy family greige rule — and her hair is doing its own thing.

At Shiv’s mother’s wedding in Tuscany, she appears first in a peculiar cerulean Chiara Boni halterneck cocktail dress and, finally, in a now notorious cap-sleeved Ted Baker bodycon midi dress.

Both gowns are tight, ill-fitting, and more overtly sexy than her looks in previous seasons. The Ted Baker dress costs less than $300 AUD, which is only weird if you’re a member of the Roy family and at your mother, Lady Caroline Collingwood’s wedding in Tuscany. The choice distressed fans and generated plenty of headlines.

Fans speculated she may be pregnant, having a nervous breakdown, or selected the dress as an intentional insult aimed at her mother. If it was an insult, it was ill-timed given the high-stakes situation the siblings found themselves in during the season finale. It may have foreshadowed a poorer choice she made later in the episode: confiding in her husband about her decision to make a move against her father.

Either way, the gown “capped off” the most emotionally and stylistically challenging season for Shiv.

Roman Roy, Blushing

Roman Roy, serving pink before he's served his demise.
Image credit: HBO/Binge

Raised in the “dog pound”, Roman Roy is superficially the most chaotic Roy sibling — but he was also the most bullied growing up. Unlike his three showboat siblings, he has learnt to fly low sartorially and deflect emotionally. Despite his “slime puppy” status, we rarely see him veer from a wardrobe of practical steel Rolex watches and unobtrusive pale blue shirts throughout the series. 

In the season 3 finale, he breaks with his signature look, wearing a blush pink shirt to his mother’s wedding. Roman is their mum’s favourite child and is most distressed by her remarriage. He’s also getting his first taste of his dad taking him seriously, something that’s dangerous for any Roy kid. The pink shirt flags his vulnerability. “Succession” clothing-coding never lies. Roman is the most emotionally devastated by the events of the season 3 finale, as he begs his dad and Jerry for reprieve and discovers his mother’s betrayal. While he’s probably the most likely sibling to return to the fold quickly, for now, the slime puppy seems shattered, and his pink shirt is retired.

We have no doubt there will be more crushing fashion faux pas before “Succession” season 4 is over, so stay tuned and we’ll keep you updated as they roll in.

Read More POPSUGAR Succession

Succession Season 4 Starts Monday, 27th of March. Stream it on Binge.

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