The 21 Greatest Fits in ‘Succession’ History

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)

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.