Kendall Roy’s Style Evolution on ‘Succession’ Is Meaningful

Photography by David M. Russell/HBO

The question is, will it be a winning one?

By Natalie Michie

Date May 26, 2023

Nothing is ever really right in Succession, but these days, the air feels particularly ominous. Waystar’s future is uncertain. Sibling rivalries are reaching a fever pitch. And democracy is in a state of peril thanks to an impending fascist president. As the series finale approaches on May 28, the question of who will become CEO is weighing heavier than ever. In spite of it all, Kendall Roy seems to be — for the first time — thriving. And his style evolution reflects it.

RELATED: The Subtle Flex of Kendall Roy’s Baseball Caps

Photography by Macall Polay/HBO

When we’re introduced to the second-eldest Roy sibling (portrayed by Jeremy Strong) in season 1, he looks like he’s playing dress-up. Wearing a fitted suit and tie, he sits in the backseat of a chauffeured Mercedes Benz blasting music on his headphones and aggressively punching the seat in front of him. As he pumps himself up to act like a corporate boss, the effect is that of a nervous boy-turned-king. Although armed in a well-tailored outfit, the worry in his eyes give him away: Kendall is out of his depth. And this is a theme for him.

Photography by Craig Blankenhorn/HBO

Kendall’s central conflict in Succession is that he overestimates his abilities, particularly in trying (and failing) to beat his dad. Consequently, his clothes play into his veneer. From his penchant for Tom Ford jackets to his collection of exorbitant baseball caps, Kendall values high-end labels, costume designer Michelle Matland told Vogue, because they help him define who he is. But over the course of the show, it’s obvious that Kendall isn’t quite sure. This is evident in season 1, after a series of failed coup attempts. At Shiv’s wedding, Kendall embarks on a search for drugs, resulting in him inadvertently killing a waiter. His toxic dependence on his dad only intensifies after revealing to him what he’s done. Logan likes when Kendall is weak, and this is ammunition.

Photography by Peter Kramer/HBO

Throughout the following seasons, Kendall’s changing appearance reflects his tumultuous mental state. In season 3, he’s the most unstable yet. Struggling with addiction, ridden with guilt, and feeling generally incapable, he’s no longer vying to emulate the boardroom uniform of his father. His hair gets shorter and patchier, resulting in an inevitable buzz cut. This reflects his split from his dad, said Angel De Angelis, the head hairstylist for Succession, to Coveteur.

Photography by Graeme Hunter/HBO

But even when he’s working against Logan, he’s constantly at war with the independent “woke” visionary he wants to be and the love-seeking neglected son that he is. He values street-style staples like baseball caps, fresh kicks, bomber jackets, and chains, but even his most casual pieces aren’t listed below a few hundred dollars. He’s forever trying to align himself with the culture, without really knowing what it is.

PHOTOGRAPHY COURTESY OF HBO

The mission to prove himself comes across in his relentless efforts to “go big.” When he rapped at his dad’s 50th work anniversary in season 2 (“L to the O G” ring a bell?), he wore a Logan Roy–themed baseball jersey. When he threw himself an absolutely unhinged birthday bash in season 3, he donned a bright green Prada turtle neck, a Gucci bomber, and an ostentatious gold chain. Most recently, while fudging the numbers of Waystar’s “Living Plus” program in a presentation to investors, Kendall took the stage in a custom Tom Cruise-inspired flight jacket. With nearly everything he wears, he’s playing pretend.

Photography by Macall B. Polay/HBO

And yet, in the fourth and final season, Kendall looks more confident than ever. In episode 5, the opening scene recreates his season 1 car-ride introduction. He’s still sitting in the backseat of a window-tinted car, but this time, the music plays on the radio while he nonchalantly scrolls through his phone. His eyes are shielded by sunglasses, and his dress shirt has a few buttons undone and no tie. He looks relaxed and decidedly at ease.

Now, Kendall is planted firmly against his dad — a stance that only gets easier after Logan passes. With the patriarch out of the picture, Kendall is no longer trying to please him, he’s becoming him. In the last few episodes alone, he’s manipulated an emotionally unstable Roman, he’s backstabbed his siblings, and he’s threatened to take his kids (who he never sees) away from his ex-wife. Logan would surely be proud.

Photography by Macall Polay/HBO

But his transformation into the image of a true cut-throat CEO takes place in episode 9. Arriving at Logan’s funeral in a Loro Piana cashmere herringbone overcoat — priced at a humble $8,895 — he’s dressed to take the thrown. After Roman chokes at the podium, Kendall steps in and saves the day, delivering a speech rich with imagery of rebirth. Afterwards, while divulging his plans to screw the GoJo deal and “rule the world,” his collar is popped just so, asserting dominance and emphasizing his newfound severity.

Photography by Macall Polay/HBO

Kendall has never been known as the smartest person in the room. But the must-have trait of a CEO, as evidenced by Logan, is not necessarily being the best, it’s the art of acting like you are. As the future head of Waystar hangs in the air, Kendall’s dressing charade has not ended. He’s still pretending. It’s just that now, he also seems to have himself convinced. That may be all it takes.

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