Kendall Roy’s 10 Best Outfits of All Time, Ranked
Plain Margiela T-shirts that cost almost as much as your rent, if not more. Suits for the price of a car. Baseball caps and sneakers and sunglasses, completely logo-less, that look so basic, they could be any affordable essential—only, they aren’t. This is the wardrobe of television’s one and only Kendall Roy, maybe-heir to Waystar Royco in Succession, definite style icon in my books.
Viewers (and, at this rate, probably non-viewers too) of Succession know that the billionaires on the show are all about understated luxury—”stealth wealth,” if you will. No branding. No logos. Insanely expensive, nonetheless. I’m talking cashmere baseball caps that are a few hundred dollars, suede moccasins that I’d be afraid to step outside in.
There’s a certain lowkey flex to the ultra-wealthy not needing to slap flashy prints and designs and monograms on their staple pieces: they may look like basics, but everyone knows they’re not spending less than a few hundred on a single garment. Those who do enter the circle of the Roys with flashy designer branding are ridiculed for their tastes, ostentatious and tacky in the face of such understated luxury—RIP, Ludicrously Capacious Bag Girl.
The beauty of Kendall Roy is that, as far as Succession characters go, he has a definitive style. He’s not Roman Roy, with an ever-present, barely-ironed button-down and trousers, nor is he Cousin Greg, bumbling around in awkwardly-fitting formalwear. Kendall’s suits are always sharp and sleek. He loves a beige knit and a gold chain and some fresh kicks. His casual wear can best be described as hypebeast-adjacent, elevated streetwear that doesn’t contain a single item under, oh, $400? And that’s just for the T-shirts. Kendall has the wardrobe of a billionaire, sure, but one who still has personal style. He’s not boring. He’s a cool guy who wears cool clothes—but subtly.
Four seasons into Succession, and we’ve seen plenty of iconic Kendall style moments, from his most dressed-up to his most dressed-down. There’s the fit he wore when he was having a mental breakdown on the yacht, for instance. Then there’s the fit he wore when he was having a mental breakdown at his mother’s wedding. And we can’t forget the fit he wore while having a mental breakdown at his own birthday party! Oh, Kendall. Maybe luxury is best paired with a panic attack? Either way—these are the very best of the best of Kendall Roy’s outfits, ranked.
#10. Sad boy hours (on a yacht)
I love this picture of Kendall so much, it’s my profile photo on Slack. Look at him—pathetic! He’s brooding in solitude on his family’s yacht, so naturally, he needs to brood with expensive headphones and almost-as expensive sunglasses on. The chunky headphones are definitely a major vibe, when we know this guy owns something smaller, like, say, AirPods. But he’s leaning into the manic pixie dreamboy thing and going the retro route, of course. And leaving the sunglasses on adds to the sullen look, contrasting his pale pink button-down. It’s giving drama!
#9. Impromptu bachelor party dressing 101
This is one of my favorite Kendall outfits, because he just looks fucking cool. He’s wearing a graphic tee by Enfants Riches Déprimés that depicts an orgy (and is now sold out everywhere). He’s thrown on a sharp blazer atop it. This is Kendall at his prime, Kendall on top of the world, Kendall not saturated in very sad shades of beige or over-the-top designer fits (we’ll get to those in a minute).
#8. Kendall after hours
What does a billionaire ousted from his company wear when he’s plotting a new company that’s best described as “Substack meets MasterClass meets The Economist meets The New Yorker“? If he’s Kendall Roy, the answer is a lot of beige, and a lot of chic, ready-to-wear designer pieces. I’m talking full Tom Ford on the torso, with Gucci sneakers that have monogramed soles. The styling here is on point: Kendall certainly knows how to layer up, if nothing else, and looks cool and casual (but not inexpensive) while doing it.
#7. “Hey, Buddha, nice Tom Fords.”
Roman may have been quipping at Kendall when he said “Nice Tom Fords,” but he wasn’t lying, really. They are! The suede sneakers might run you up about a band, but, hey—take a page from Kendall’s book and pair them with a matching Tom Ford hoodie that costs even more. Real Buddha behavior.
#6. Working hard at hardly working
What do you wear to pray on your family’s downfall? If you’re Kendall Roy, it’s a suit-and-baseball-hat combo. In “The Disruption,” an estranged Kendall stormed Waystar Royco ready to kill and wreak havoc, and he obviously had to find a balance between businesswear and incognito attire to do that. He did, too, with a Loro Piana baseball cap to match his navy suit. Casual(ish) but still cashmere, this is the baseball cap for billionaires looking to cause a disruption. Plus, he looks almost like a classic, Season 1 Kendall here: suited up, ready to make some noise. This is even better, though, because Season 1 Kendall wouldn’t wear a baseball cap to work. He’s edgy! He’s free! And it’s sure as hell reflected in his clothing choices.
#5. Weddingcore, or, perhaps, funeralcore
Leave it to Kendall to show up to his brother’s wedding in a suit way more expensive than the one the groom himself is wearing. While Connor looked elegant for under $1000, Kendall looked ready to kill in a sleek, sharp Brioni suit that costs a whopping $11,500. Yeah, you read that right. This is perhaps the most put-together Kendall’s looked in years, which is ironic, considering what happens next in this episode. It’s a good thing he brought his Jacques Marie Mage Zephirin sunnies—they do good at hiding tears when you find out at the wedding that your father died. Yikes.
#4. At brunch, in denial, still serving
In the season finale of Season 3, Kendall is at an all-time low. Guilt is getting to him. He spent the last few seconds of the previous episode face-down in a swimming pool, beer in hand. And when confronted with his almost-drowning, the man is in pure denial—he doesn’t need an intervention! Look at the rest of the Roys! There’s a lot going wrong for Ken in this episode, but one thing going absolutely right is the $25,000 gold pendant he pairs with a plain Maison Margiela T-shirt and Jacques Marie Mage sunglasses (the pendant also made an appearance in “Too Much Birthday”). He looks like a man who has lost everything, at this point, except his taste in fashion. You know things can’t be that bad if Ken is still bringing out the gold chain, after all.
#3. Not enough birthday
This was a great episode for Kendall’s style, from planning his party to rehearsing for it to actually being at the birthday party. And though the birthday itself didn’t go as planned—at least Kendall looked good the whole time. While rehearsing his musical number with Naomi, Kendall did not come to play, wearing head-to-toe, flashy designer: a Gucci bomber, Prada geometric turtleneck, and Gucci Ultrapace Low-Top Sneakers. Stealth wealth is nothing in the face of a man with unlimited money and a bit of birthday excitement, clearly.
#2. Confessions of a killer
If you have to confess to killing a kid at your sister’s wedding, you better do it decked out in Loro Piana at your mother’s wedding. For all his faults, Kendall knows how to do drama in style. He leans into the Tuscan look with a full Loro Piana suit, complete with suede moccasin loafers and a billowy linen shirt. He looks like a man on vacation! A man at a wedding! He looks a lot more chill than he feels, and is absolutely acing summer wedding style. Nothing is less than a few hundred dollars, obviously. But there’s a price to pay for everything—unintentional murder’s costs about as much as Loro Piana does.
#1. The ultimate party-planning drip
One thing about Kendall Roy—he’s gonna dress for the occasion. Even before his actual birthday party, Kendall was in Gucci drip (with a chain on! Iconic!) for the planning sesh with his buddies, blunt in one hand and iPad in the other (those aren’t part of the outfit, but they certainly add to the aesthetic). The Billionaire Birthday Boy looked cool as hell in a green cashmere turtleneck from Gucci, which is no longer available, but a similar option is. This is, admittedly, a hard look to pull off, but Kendall Roy does it as he does very few things: with ease and elegance.
Trishna Rikhy is the Associate Style Commerce Editor at Esquire. Previously, her writing has appeared in Vogue Runway, PAPER Magazine, V Magazine, V MAN, and more. She is based in NYC, but can probably be found wherever the strongest cup of coffee is.
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