Kendall Roy: Hat Boy

Look at this business boy and his business baseball hat! Photo: Macall Polay/HBO

We are four episodes in to season three of Succession, and already we’ve had an abundance of revelations. Papa Roy is continuing to mask his declining health. Tom is willing (??) to offer himself up as the fall guy for Waystar Royco. Greg apparently has the balls to ask Logan for a “COCA-COLA” to go with his rum. Most importantly, Kendall is a hat boy now.

Chin up, hat boy! Photo: HBO

I suppose Kendall’s always been something of a hat boy. We’ve seen him in his sad-boy beanie era. There was the brief appearance of both an ushanka and a summertime fedora. But to wear a baseball hat with a suit, something Kendall does when he shows up unannounced at Waystar’s offices? Powerful. Inspiring. Provocative. It is work casual at its peak. It says, I mean business but could catch a baseball if I needed to. Imagine a reprise of Kendall’s rap ode to his father, but this time, he’s got on a little hat!

Something about an adult man in a baseball hat makes me want to hold his hand before he crosses the street … and then, once we’re safely on the other side, immediately slap his wrist. It’s an oddly arresting image — very after-hours finance bro. I both want to avoid this man at all costs and ask if he needs some orange slices as a snack. I will deny ever writing this, but Kendall Roy in a baseball hat and suit is the only man who could call me “mommy” and get away with it.

Aw, look at him doing business like a big business boy! Photo: HBO

The baseball hat and suit combo is truly the Kendall Roy special. It is at once pathetic and cocky, overly formal and far too comfortable. It’s the stylistic embodiment of his character’s extremes. It’s also a very good Halloween costume, if you want to keep that idea in your pocket for another 11 months.

Did you know that being a hat boy is hereditary? Photo: HBO

Truth be told, it’s a little surprising that Kendall has chosen a logo-less hat as his default. I keep expecting him to show up in a Chance the Rapper “3” snapback or a baseball cap emblazoned with THE FUTURE IS FEMALE. Perhaps that is in an episode to come. Or maybe, in a future episode, all members of the Roy family wear hats as a fun bonding experience or for another weird magazine shoot. Who cares! Just put them all in matching caps! The future is hats!

Kendall Roy: Hat Boy