The Style of Succession

As the fresh, young, energetic face of the next generation of Waystar Royco leadership (or so he hopes), Kendall Roy’s look is a hybrid of boardroom classics and high-end streetwear. Having ditched his infamous Lanvin sneakers following an embarrassing incident in season 1, Kendall seems to have mostly learned his lesson this season, sticking to dark, tailored suits and white shirts with small point collars (usually worn sans tie). Kendall’s best fit of the season so far may be the TOM FORD corduroy trucker jacket he wore for his ill-fated lunch in episode four. His biggest misstep this season? Wearing a baseball cap with a suit.

An outsider to the Roys’ world of power and money, Greg has slowly wormed his way into Waystar Royco’s corridors of power, and proved himself a surprisingly shrewd tactician. He has come a long way both in business and in style. Whereas in season one he comes into the fold wearing likely the only blue blazer he has – this year Greg is dressing the part, thanks to a wardrobe of dark suits tailored to his 6’ 6” frame, with sober black cap-toes in place of his former deck shoes. Greg still has a lot to learn however, as we discover when he buys an outrageously overpriced grey market Rolex (which may or may not actually work).

Ah, poor Tom. He thought he had the golden ticket when he married Shiv Roy, only to be forced to take the fall for Logan’s cruise ship misdeeds. Tom’s wardrobe is that of a man who is trying very hard to fit in with his more wealthy new family. He can’t get away of the more casual more lived-in style of say, Roman, and so he goes a little bit extra with pin stripes and matching ties and pocket squares meant to signal that he belongs.

For someone with a prison sentence hanging over his head, however, Tom still manages to look sharp in his prep-approved wardrobe of conservatively cut suits from ZEGNA and Loro Piana, quilted vests from Moncler and the occasional pair of red trousers.

This venture capitalist has his sights set on control of Waystar Royco, but (unlike everyone else on this show) at least he’s honest about his intentions. Stewy’s style is befitting of a guy with the world at his feet, particularly his penchant for dark turtlenecks under dark suits.

Introduced this season and played by the always-stylish Adrien Brody, Josh Aaronson is a billionaire stakeholder in Waystar Royco who is playing both sides to recoup the $350 million loss he incurred when the company’s stock tanked. While he lives in a beautiful beach house on a private island tastefully outfitted with modern furniture and art, his personal style leaves much to be desired. When Kendall and Logan arrive to discuss the future of their company over an extremely awkward hike through the dunes, Josh greets them in a laundry hamper’s worth of layers. In what might be the season’s most audacious fit – a sartorial expression of “You need me more than I need you,” – Josh takes the meeting in a down vest worn over a hoodie, worn over a cardigan, worn over a button-down, worn over a long-sleeved tee (deep breath) plus a beanie and a scarf for good measure. Josh Aaronson may turn out to be an extremely savvy businessman, but where layering is concerned he clearly needs help.