The 21 Greatest Fits in Succession History

Costume designer Michelle Matland weighs in on the show’s most memorable style moments.
The 21 Greatest Fits in 'Succession' History
Photographs: HBO; Collage: Gabe Conte

Succession was a show about many things: money, power, destiny. It was also a show about clothes—and namely, how the wealthiest people in the world wear them. 

Charting the fashion on Succession became a cottage industry for fans of the recently departed HBO series, spurning a fastidious Succession Fashion” Instagram account, a weekly blog series penned by the New York Times’s Styles desk, and myriad stories breaking down the potential motivations behind the characters’ wardrobes; the cultural significance of “stealth wealth” and “quiet luxury”; and identifying the high-end (and sometimes low-end) brands that ended up in the Roys’ fictional closets. 

After polling a few of my GQ colleagues on their favorite style moments from the show, I spoke to Michelle Matland, the show’s Emmy-nominated costume designer, about the process behind them. Matland provided a final word on how she and her team costumed this very particular sect of the incredibly wealthy—or, as she puts it, “those who can afford to choose to not have a giant Gucci on their tush, you know what I mean?”

While the show’s biggest scenes were often the most stressful for Matland and her team—having to dress dozens of characters and extras to fit a certain setting—they were also ripe for delivering her personal favorite Succession fashion moments. “It’s weddings, funerals, birthday parties where we get to indulge ourselves,” Matland says. “It’s always about how much homework we [got] to do, or how much time we could take spending on the details.”

From the style extravaganza that was Kendall’s “Too Much Birthday” party in season 3 to the Roys’ many fashion flops and finesses, here are the 21 best fashion moments from Succession, in its entirety.

21. Roman Roy’s Walmart T-shirt (season 4, episode 10)

Courtesy of HBO

Of Succession’s major players, Roman (Kieran Culkin) is perhaps the least concerned with fashion, except when clothing can be used as a barometer to determine someone else’s patheticness. But when we find Roman hiding out in Barbados in the series finale, his little striped T-shirt (which, as fans quickly sussed out, came from the boys section of Walmart) is perhaps the most feeble thing he’s ever worn—but also the most comfortable.

“The T-shirt and shorts that Roman wears in the end [make] him so childlike and kind of fragile,” Matland says. “Almost pathetic in the costume, and yet we see him really battle that.”

20. The “ludicrously capacious” Burberry bag (season 4, episode 1)

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In just one scene, set at what would be Logan’s last birthday party, the show’s final season premiere gave us two of the series’s most potent Twitter jokes: Greg (Nicholas Braun) and Tom (Matthew Macfadyen) referring to themselves as “the Disgusting Brothers,” and Tom deriding Greg’s date’s gaudy Burberry tote as a “ludicrously capacious bag.” 

“What’s even in there?” Tom goads. “Flat shoes for the subway? Her lunch pail? Greg, it’s monstrous. It’s gargantuan. You can take it camping. You can slide it across the floor after a bank job.”

This, Matland says, was by creator Jesse Armstrong’s design: “It just is funny that [the audience] latched onto the bag as this icon, which is so interesting because that’s exactly what Jesse had written. And he obviously knew his audience 100%, because everybody was like, ‘Oh my God, that bag.’”

19. Shiv Roy’s lefty season 1 wardrobe

Courtesy of HBO

It’s easy to forget that when we first meet Shiv (Sarah Snook) in season 1, she was dressing (and behaving) with an entirely different set of motivations. She’s a political advisor for a left-leaning Democratic candidate who, as Matland reminds us, “does not want to be seen as a Roy.” 

Season 1 Shiv wears her hair in loose ringlets, drapes paisley scarves around her neck, and, in the pilot, rolls up to the family baseball game in a jaunty, oversized Fair Isle Christmas cardigan-turned-grief sweater. Feels like a false memory.

18. Kendall Roy’s “L to the OG” baseball jersey (season 2, episode 8)

The idea that Jeremy Strong’s Kendall Roy hid that damn novelty jersey underneath Strong’s real-life Emmys suit (in brown, obviously) until it was time to rap over his Squiggle-cooked beat at his dad’s workiversary party in Dundee is absolutely diabolical. He is not, and never was, a serious person…but he does love custom merch.

17. Cousin Greg’s boat shoes and parka (worn throughout season 1)

Courtesy of HBO

Greg Hirsch, who is the Roys’ first cousin once removed, has perhaps the series’s most craven glow-up: Cousin Greg starts the show in a rat costume, a schlubby parka, and thrift-shop boat shoes, and by virtue of being Tom’s number-one boy, ends up wearing high-end business attire befitting of the world’s most overpaid assistant.

By the finale, Matland points out, “Tom is wearing $8,000 suits and Greg is wearing the next [level] underneath that, so maybe $3,000 suits.”

16. Karl Muller’s esteemed prep (season 4, episode 8)

Courtesy of HBO

This man’s been in the corporate fashion trenches longer than any of these Roy-spawn dingbats have even been alive. Look at those clashing stripes! Karl (David Rasche) and Frank (Peter Friedman), a.k.a. the Frick and Frack of the Waystar C-suite, have some of the best suiting senses of the whole show.

15. Kendall’s gigantic golf umbrella (season 1, episode 3)

Courtesy of HBO

This one’s for the real heads. (Ken’s umbrella, for the record, is from Procella.) Bonus points for Stewy’s (Arian Moayed) cutie knit tie.

14. Lukas Matsson’s gold Needles jacket (season 4, episode 7)

Courtesy of David M. Russell for HBO

Succession was, in many ways, a show about jackets. So it’s only fitting that Lukas Matsson—Alexander Skarsgård’s tech edgelord, who trolls the Roys’ pre-election-day party by pulling up in a post-drip Needles bomber and Kyrie Irving Nikes—ends up dunking on Kendall and his Tom Ford suede jacket in the end.

13. Logan Roy’s cable knit cardigans (worn throughout)

Courtesy of HBO

Logan Roy (Brian Cox) is a no-nonsense dresser: he wears a suit at the office, and a cable knit shawl cardigan at home. He wears a navy one in the show’s opening credits, which Matland imagines he’s had for years.

“He has many of them. Everybody buys them for him for his birthday and Christmas and he has a closet full. He probably has his four favorites,” she says. “And they’re just to say, ‘I’m home. I’m off.’ He has no pretense because he has nothing to prove to anyone…He’s the king at home. He can take the crown off.”

12. Kendall’s Lanvin sneakers (season 1, episode 8)

During his half-baked stint as a disruptive angel investor, Kendall cops a pair of calfskin Lanvin sneakers he hopes might impress a couple of artsy tech startup founders. “Oh, fuck yeah,” he says, holding up the shoes in the backseat of his car while a Run the Jewels song plays. He does not land the deal.

Kendall wears many designer sneakers throughout the series, many of which were hand-selected by Jeremy Strong (whom Matland says “there’s not a detail that gets past”) to directly reflect Ken’s headspace. This Lanvin pair, Matland says, conveys his insecurity: “He wants to be part of the hip crowd and speak that language with clothing, and it ends up backfiring where they’re a little bit too ostentatious, which was obviously not his intention.”

11. Gerri Kellman’s boat ensemble (season 4, episode 3)

Courtesy of HBO

J. Smith Cameron’s Gerri Kellman has one of Matland’s favorite wardrobe arcs, because she “becomes much more stylish as the seasons go on, and much more high-end luxe.” As we learn how powerful Gerri actually is, her clothes become “more form-fitting, less boxy, less masculine, less corporate.” This structured Scanlon Theodore suit she wears to Connor and Willa’s wedding, for example, feels like corporate noir, which in turn makes her loosened-up post-Logan style that much more alluring. As British Vogue put it, death becomes her.

10. Naomi Pierce’s Proenza Schouler set (season 3, episode 7)

Courtesy of Macall Polay for HBO

Naomi Pierce (Annabelle Dexter-Jones) is Succession’s “It” girl. She is the show’s most objectively stylish character, with a socialite’s wardrobe full of monochromatic pieces from brands like Tom Ford, The Row, and Proenza Schouler—the latter of whom made this perfect white loungewear set Naomi wears while a spiraling Kendall preps for his doomed 40th birthday bash. (The strapless gold-buttoned top she wears to the actual party is also Proenza.) 

Matland has a great backstory for Naomi, which really puts her wardrobe in context. “She knows that when she gets out of the car, everybody’s going to want to have a piece of her. She knows that at any club, at any restaurant, she will get a table,” Matland explains. “She could be dressed in 10 minutes. She throws on a lip gloss and maybe a tiny bit of blush, or maybe not. She puts some goo in her hair, she grabs her handbag, and forgets her credit card. She doesn’t have to worry about it. She probably doesn’t wear underwear, you know what I mean? She doesn’t waste the time. ‘I’m going out. See ya.’”

9. Matsson’s luxury Swedish streetwear (worn throughout season 4)

Courtesy of HBO

Matland imagines that Ebba (Eili Harboe) does all of her boss’s shopping for him—just as she does most everything else as GoJo’s head of communications and Mattson’s sometimes-lover. If he needs clothes, he’ll send Ebba and a driver to the shops and she’ll return “with bags and bags of luxury items that look like you could get them at Walmart.”

Whether it’s the hulking, “Evil Kermit” Fjällräven anorak he wears in Denmark, or the pale green Acne sweatsuit he lounges in while Shiv’s losing the deal, Matsson’s annoyingly casual Swedish streetwear was a star player in the show’s finale season. Think of it as the “I really don’t care, do u?” jacket for the tech scion set.

8. Roman’s workout headband (season 1, episode 3)

Another worthy deep cut: the little workout headband Roman wears (à la Colin Farrell) when he briefly enlists a hunky trainer to help him get CEO fit in season 1. Here’s a clip of the two of them stretching, or you can just take our word for it?

7. Kendall’s “Too Much Birthday” Gucci wardrobe (season 3, episode 7)

Courtesy of Macall Polay for HBO

It’s Kendall’s 40th birthday party, and he’ll wear three different Gucci ensembles if he wants to.

“This is his big moment of frivolity,” says Matland. “His big enjoyment of the world. He’s on a high. Everything is coming to him and he’s having a crowning moment.” While we know this moment inevitably falls apart, Kendall psyches himself up by wearing two different embroidered silk bomber jackets (see #10) plus a hilariously svelte green turtleneck from the Italian house, which kinda makes me wonder what his eBay search history looks like.

6. Connor Roy’s “Too Much Birthday” jacket (season 3, episode 7)

Courtesy of Macall Polay for HBO

That said, my personal favorite jacket moment in “Too Much Birthday” is when eldest brother Connor (Alan Ruck) refuses to remove his knightly Canali coat inside the party, which finally pushes Kendall to the brink. How quickly “This is nothing but can we get Connor to lose his coat? Yeah, it’s nothing. He’s souring the vibe” can become “Take your fucking coat off!”, huh?

5. Shiv’s backless Gabriela Hearst turtleneck dress (season 2, episode 8)

Courtesy of HBO

Shiv’s wardrobe had already become a fan favorite by season 2, but the exquisite, mind-boggling backless wool turtleneck dress (!) she wore in episode 8 (“Dundee”) sent everyone over the edge. We wouldn’t know it until it was too late, but this was Shiv flying closest to the “future CEO” sun; once she lost her footing with her dad, her personal style only got stranger and more inconsistent.

4. Tom Wambsgans’s beige turtleneck (season 2, episode 1)

Like his wife Shiv, Tom favors turtlenecks—though his always tend to make him look too green and/or constricted. (Perhaps because he’s always metaphorically sticking his neck out?) But the oatmeal-hued Larusmiani cable knit he wears in the season 2 opener, which takes place at the Roys’ Hamptons compound, is even more delicious in hindsight. He may look a little like a WASP-y narc, but that’s what’s going to make him Waystar’s next CEO in the end.

3. Kendall’s Loro Piana baseball cap (worn throughout)

Courtesy of Macall Polay for HBO

Kendall Roy’s $625 logoless cashmere baseball cap, a.k.a. the item that launched a thousand explainer articles/TikToks about Succession and “stealth wealth”—including one on this very website! According to Matland, the show’s costume team never used that term during production, possibly because it didn’t crop up until the show’s final season. “It was never in our lexicon or vocabulary,” she says. “We had studied that percent [of the uber-rich] as best we could by following them into stores and trailing them down the street when we had the opportunity.” 

2. Josh Aaronson’s many layers (season 3, episode 4)

Courtesy of Macall Polay for HBO

Adrien Brody guest-starred in a single episode of Succession’s third season, playing the nouveau-beatnik billionaire shareholder Josh Aaronson, whose four-percent Waystar stake compels a feuding Logan and Kendall to pay a visit to Josh’s secluded island (which they fly to in separate PJs, of course). When the three gather for a seaside lobster lunch that inevitably goes uneaten, we get a closer look at Josh’s mind-bogglingly layered “chill guy” outfit: puffer vest, zip-up hoodie, cardigan, button-down shirt, cardigan, T-shirt, scarf, beanie. An eight-layer dip of gorpcore.

With Aaronson, Matland says, “it’s the same idea as with Matsson, where the pretense is that they take no pride in their clothes, that it just happens naturally. It’s this organic comfort zone that they don't spend time worrying about what they wear. They can be barefoot. They could have four layers on. They could wear sweatpants.” The Roys, on the other hand, have “this pretense of having to wear a costume.” Aaronson or Matsson’s aggressively relaxed style, then, makes them feel uncomfortable and overdressed, as if to say, “You are part of the bureaucracy and you don’t have choices like I have because I am free to be me.”

1. Shiv’s high-waisted trousers (worn throughout)

Courtesy of HBO

For all of the slack-jawed love bestowed upon Shiv’s backless turtleneck dress (see item #5 on this list), these high-waisted trousers were her true signature garment. The dress was a showstopper, but her pants were a constant, reliable companion that kept Team Shiv afloat.

When Shiv gets back into the family business in season 2, her corporate wardrobe receives what Matland calls its “Katharine Hepburn moment”: the chic bob haircut, the architectural suits, the high-waisted pants. “It’s very feminine, but also with a masculine ilk to it,” she says. “I think Shiv pulled that off so often with just a simple turtleneck and a great fitted structured suit on her, with a high waist and long legs and her beautiful face.” Amen to that.