How To Dress As Your Fave ‘Succession’ Characters For Halloween

For those of us who have made the WFH transition in the past few years, minus an occasional office cameo, wearing full business attire can feel like cosplay at this point. After all, there’s little need for heels or dress shoes when your boss only sees you from the waist up. Even wearing a tie for a Zoom call can even feel a bit gauche. (A very Tom Wambsgans move, if you ask me.) But, before you start selling your suits on Facebook Marketplace, you might be overlooking a very important conference on your calendar: Halloween parties. That’s right — ‘tis the season for Succession Halloween costumes.

The highly anticipated Season 3 of Succession premiered on HBO on Oct. 17, meaning there’s more drama to mine for your Halloween party next weekend. Whether you’re ready to go all out with an “L to the OG” jersey for Kendall, or just want to throw a raincoat over your button-down to dress as Cousin Greg, the best part about Succession costumes is that they’re fairly easy to recreate with whatever work clothes you can find. (Of course, the price point may vary a bit from the Roys’ all-designer closets.) You may not be in competition for the title of Waystar Royco CEO, but you will be a top contender at your costume contest. So, suit up and get to work. Just don’t forget to bring your conscience with you.

Kendall Roy

Waystar Royco heir Kendall Roy is a lot less effortlessly cool as he is calculated and cringe most of the time. But he does make his attempts to have standout style with ridiculously expensive suits. If you don’t have a brown Brunello Cucinelli tux or flashy sneakers lying around, dressing in preppy earth tones is key. Or, of course, you can opt for the most recognizable: an “L to the OG” jersey with a brown bow tie, brown pants, and brown dress shoes.

Shiv Roy

Very few Succession characters’ style are as talked about as Siobhan “Shiv” Roy. Having made a major transformation from her relaxed style and long tresses in Season 1, Shiv’s sleek bob and tailored pantsuits have marked a major shift in her trajectory as a hopeful successor to her father. Take your pick at her two alter egos of fashion, or, if you’re feel really dedicated, make a costume change by shrugging off your baggy sweater and long wig to reveal a bob and suit.

Roman Roy

It’s easy to flex your wealth with an expensive wardrobe. But nothing says, “I’m filthy rich,” quite like wearing an expensive outfit in the most careless way possible. To capture the casual cockiness of Roman, slick back your hair and wear a navy blue button down with a grey wool coat. Extra wrinkles, hold the tie.

Connor Roy

Though eldest son Connor Roy tries his best to remain outside of the internal power struggle of his family, he has his own appetite for power in different ways — and this shines through in his style. Where his siblings dress to impress in business attire, Connor dresses to express his difference in an equally lavish, “I live on a farm” way. Think: sweater vests, crushed velvet jackets, and gingham button-downs.

Logan Roy

Waystar Royco founder Logan Roy’s style is as “old money” as it gets, complete with bespoke suits, ascots, scarves, and cable-knit sweaters. The layers that line Logan’s cold-blooded body also make this a great option if you’re sick of shivering the night away in your Halloween costume.

Gerri Kellman

It takes a lot for an outsider of the Roy family to still be a power player at Waystar Royco. Enter: Gerri Kellman. We can always count on a cutting one-liner from the observant Gerri, just as much as we can count on her to arrive in her own brand of sophisticated chic. Wear a long silk blouse with a gray overcoat and accessorize with glasses. If you’re feeling like stirring the pot, you can always make this into a couple’s costume with Roman.

Cousin Greg

If you really want to pull off Cousin Greg, you may want to opt for some stilts to match Nicholas Braun’s 6’7” stature. Unlike his cousins, Greg Hirsch doesn’t come from money — well, as much money. But, with aspirations to join Waystar, he tries his best to play the part. Few outfits capture this dissonance quite like his blue button-down and khakis paired with a baggy green raincoat.

Tom Wambsgans

Here’s the counterpart to a memorable, albeit strange, couple costume with Shiv. The only thing midwesterner Tom Wambsgans loves more than his wife Shiv is her family’s power. Tom’s clunky attempts at fitting in with the Roys are often the very reason he sticks out like a sore thumb -- rather than trying to fit into a box at Waystar Royco, Tom sees to try to be a box with his angular suits. The key to transforming a regular suit and tie into a Tom costume is trying way too hard. (Think: polished shoes, perfectly ironed clothes, gelled hair, etc.)