All the Hidden Metaphors Behind Succession’s High-Stakes Fashion Choices

All of the Roy siblings are wildly lacking in self awareness and out of touch with the average person’s reality, but Kendall Roy (played by Jeremy Strong) seems to always win the Number 1 Boy title in the race to hypocrisy. One example: in episode 2 of season 4, Kendall tells his siblings, “In Buddhism, sometimes your greatest tormentor can also be your most perceptive teacher.”

“Hey, Buddha: nice Tom Fords,” Roman Roy (played by Kieran Culkin) snaps at his brother. Kendall is wearing $990 Tom Ford sneakers while lecturing his billionaire siblings about suffering.

While Roman only clocks the shoes, Kendall is also wearing a Tom Ford hoodie (worth approximately $1,390). This is a man who will unironically quote a religion with tenets of achieving enlightenment through awareness, kindness, wisdom, and spiritual development while wearing a $2k outfit.

$182,000 actually, if you’re including the watch.

Kendall Roy unwraps a pair of calfskin Lanvin sneakers while being chauffeured through Manhattan traffic. He’s going to a meeting in hopes of partnering with a hip, buzzy start-up that helps struggling artists connect with high-end art buyers. “Oh, fuck yeah,” Roy says as he peels back the tissue paper to reveal the $500+ sneakers and puts them on. It’s all he needs to impress these cool, downtown kids.

Moments later, the meeting begins and it’s instantly clear that Roy doesn’t get it. He paces around the office tossing out buzzwords and weird promises in his cool sneakers, while everyone else is professionally dressed and acting like reasonable human beings. He’s misread the room — again.

His corporate swagger and fresh-out-of-the-box hypebeast sneakers are superficial markers that can’t hide the fact that he has no idea what this startup company needs or how to win them over. “I got these sneakers on the way down here because I thought . . . you’d all be dressed like fuckin’ Bjork, and I wanted to make an impression,” he says, eventually. “So, I’m a jackass.”

Ultimately, the sneakers serve as a metaphor for Roy being bad at business and bad at people. Whatever room he’s in — and this is true for his entire existence — he will forever have the most expensive shoes, but also the crippling inability to read the room. Try as he might, Kendall just cannot escape his money or his cringe, for now.

The Roy family and their elite inner circle employ a strict policy of stealth wealth gatekeeping. Interlopers become instant targets for not adhering to the invisible set of sartorial rules the Waystar Royco crew follows.

Enter the Hall of Fame takedown Tom Wambsgans lobbed at the tragically middle-class date Greg Hirsch brought to Logan Roy’s (played by Brian Cox) birthday party in episode 1 of season 4. The young woman’s crime? Bringing a tote-sized, logo-explicit Burberry bag.

“[…] she’s brought a ludicrously capacious bag,” Wambsgans says. “What’s even in there, huh? Flat shoes for the subway? Her lunch pail? I mean, Greg, it’s monstrous. It’s gargantuan. You could take it camping. You could slide it across the floor after a bank job.” He’s offended just by being in her presence.

Costume designer Matland explained the sartorial choice in an interview with The Ringer. “We wanted her to look like she didn’t fit in, whatever was going to make her stand out in the crowd. And in this crowd, anything that was too present, too obvious was going to get her kicked out of this house.”

Choosing a bag with Burberry’s conspicuous plaid print was intentional. “We knew that [the bag] had to define what someone who is, let’s say, middle class, might aspire to help tell their story that they are moving on up. She carries this bag because she thinks it makes her look important and it backfires. We knew it had to have some sort of logo, and we didn’t want the logo to be so rarefied that she wouldn’t be able to buy it. So our goal was to drop it down to her standards of what she thinks is the most glorious and refined — but it isn’t.”

It is worth noting that the bag in question retails for over $2,800. It is an expensive bag from an iconic, legacy luxury brand that most of us would consider a privilege to own, but not the Roys and those in their .0001% orbit. To them, it’s worthy of sneers and shame. The bag itself isn’t a metaphor for gauche taste, but rather it serves as a reminder of the cruelty and callousness of the Roy family and their associates.

Shiv Roy’s (played by Sarah Snook) husband Tom Wambsgans is deeply infatuated with the Roy family’s power and wealth, but he remains an outsider. He does his best to fit in and earn the cruel patriarch Logan Roy’s affection, but is instead constantly belittled, mocked, and thrown under the bus by his in-laws and, often, his wife.

In an interview with Variety, Matland explained how Wambsgans’s on-screen wardrobe reflects that outsider status. “He’s just not an equal, on so many levels, to the people that he’s competing with. It feels almost like a competition for him,” Matland said. “And he’s a very bright man. But he was not brought up in a household of great wealth. He was not educated the way they were. And so, he is a posturer. And there is a level of a facade on him where the clothes are, it’s like Dressy Bessy, you know? It’s laid on top of the person rather than worn organically like he owns it.”

His boardroom style is, on paper, similar to Kendall and Roman Roy’s, but add on his “Dress Bessy” details of polished shoes, perfectly ironed shirts, gelled hair, and matching his tie to his pocket square — and it becomes markedly different. All those subtle details become an amalgamation that telegraph his otherness. Sure, he’s wearing a suit, but not like a Roy would wear a suit.

One piece that neatly sums up Matland’s point is the Moncler puffy vest Wambsgans wears in season 2, episode 6, an episode that takes place inside a mountain top resort at a conference for billionaires. Puffy vests have, strangely, become symbols of power for businessmen, but in a sea of black padded vests, Wambsgans’s version is extra ostentatious.

“One of the decisions that we made, for example, was when we did the big conference. There are eight million puffy vests in the world; his, of course, has to have the patch that says Moncler or whatever. He can’t get past that because those identifiable markers on the price tags are the things that make him comfortable.” By buying an expensive, flashy version of the puffy black vest, Wambsgans thinks he’ll fit in but, in reality, that try-hardness only makes him stand out more.

In season 3, episode 1, we briefly see Wambsgans in a puffy vest again but it’s much more subtle and, therefore, much more appropriate. This style evolution hints at his savviness. Wambsgans is a social climber and a suck-up who never makes the same mistake twice. Of course, he studied everyone else’s vests and made sure he bought the right one for next time.

Interestingly Matland has a theory about the popularity of puffy vests among the white-collar corporate set. She told The Ringer, “I think they wear them because they make them look tougher than they actually are. These are guys who never played football. The vests are something that make them feel bigger than they physically are.”

One of my favorite Shiv Roy outfits is this gorgeous, plaid suit she wears in season 2, episode eight to take down her new rival-for-CEO, Rhea Jarrell. Roy wears businesswear almost exclusively, but rarely does she appear in a full suit set and, even then, they’re only rendered in neutral, monochromatic shades of cream, gray, or black. Since we mainly see her in sharp blazers, pressed trousers, and silk button downs in neutral palettes, this loud and printed suit is screamingly different — a visual indicator she means business.

Speaking of Shiv Roy, her series-long fashion transformation is a metaphor for her alignment with the Roy family business and her increasingly intense ruthlessness.

In season 1, we meet Roy as the rebellious and liberal sibling. She wasn’t working anywhere near her father, instead working in DC for the Democratic presidential hopeful, a Bernie Sanders-esque character Gil Eavis. Season 1 Shiv Roy had long, romantic waves in her hair, silk blouses, warm jewel tones, and one of chunkiest, coziest sweaters I’ve ever seen.

When the wiley and weird tech barron Lukas Matsson (played by Alexander Skarsgård) arrives to “tailgate” at Shiv Roy and Tom Wambsgans’s penthouse in season 4, episode 7, he’s wearing a bit of sartorial flash rarely seen on Succession: a gold, velvet bomber jacket.

“I wanted something eccentric and crazy when it came to the jacket, something that really stood out, because the Roys are always so understated. It’s that kind of classy, downplayed, very, very expensive, but no logos, nothing ostentatious because it’s tacky,” Skarsgård told Vulture of his costume collaboration. “I wanted to give that a big “fuck you” and walk in wearing something completely different. Also, knowing that everyone else in the room would be sycophants and vultures running around the Roys, it’d be fun if Matsson comes in like a sore thumb.” A power move in the form of power dressing.

Gerri Kellman (played by J. Smith-Cameron) is the lone woman on Logan Roy’s executive board. She has survived an Everest-sized mountain of bullshit from her decades working alongside the patriarch of the Roy family. In season 1, we saw Kellman in a corporate-friendly, blend-into-the-walls palette of grays and blacks. She is muted in the shadow of Roy, firmly his underling. Through the seasons, Kellman subtly builds confidence and power. Her wardrobe reflects that evolution, peaking with the beautiful Scanlan Theodore wedding outfit she wears in season 4, episode 3.

“Gerri now has a beau and she has something to prove to Roman and the team — that she is a woman as well as a corporate phenom,” Matland told Vogue. “I think that she takes these opportunities to dress up just as seriously as she takes the uniform she wears in the boardroom. Her boardroom look has really evolved over the years, and this season, we see some very body-skimming looks that are almost mildly sexual in shape. She’s finding her way, and you have to remember that this season is all about power and who comes out on top, so everyone’s in battle mode and thinking about what their clothing is saying when they get to work.”

One of the major non-Roy characters featured in Succession is Kerry Castellabate (played by Zoe Winters), Logan Roy’s personal assistant who eventually becomes his (last) companion. She leverages her position close to the throne to get an audition for her dream job: ATN Correspondent. But we all knew that job was never actually going to happen, especially Matland.

In a conversation with The Ringer, Matland described how Castellabate’s overconfidence in securing the on-air job (thanks to her coziness with Roy) was telegraphed by the overconfidence displayed in her outfits. “They’re just on the left side of right. They’re not really appropriate for what she’s attempting to become. And the clothes just reflect how she’s not quite in the loop. The silhouettes and the colors are a little bit too much,” explains Matland. “She’s loud and proud, and it doesn’t quite work. And against the compensation for her delicate position, everyone else has sort of a classic look — simplicity, very clean cuts, minimalist. She is slightly outrageous in comparison.”

Can you tell the difference between a black $12.99 baseball hat and a $600 one? The Roy men favor Loro Piana status symbol baseball hats, made of waterproof cashmere and a logo so subtle you have to squint to see it. The stealth wealth accessory is the perfect encapsulation of the billionaire-off-duty aesthetic.

According to Matland, the very expensive hats, worn by both Logan and Kendall, are a metaphor for their massive egos and selfish natures. She explained to The Wall Street Journal that the logo-less baseball hats visually suggest “no relevant team but… team Me.”