Kendall Roy, played by Jeremy Strong, unwraps a pair of calfskin Lanvin trainers whilst 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 pair with high-end art buyers. "Oh, fuck yeah", Kendall says, pleased as punch from his black car as he peels back the tissue paper to reveal the £500+ sneakers and put them on. It's all he needs to impress these cool, downtown kids. Or not.
Moments later, the meeting begins and it's instantly clear that Kendall doesn't get it. He paces around the office tossing out buzzwords and weird promises in his cool trainers, 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 trainers are superficial markers that can't hide the fact that he has no idea what this startup company needs, wants, 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 trainers serve as a metaphor for Kendall 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.