Last updated: July 8, 2026·🔄 Guide reviewed and refreshed ahead of Halloween 2026.· By Seckin Peker

Halloween Costume Guide

Henry Sugar Halloween Costume Guide

He trains for three years to see without his eyes, wins a fortune at cards, then gives all of it away.
Benedict Cumberbatch British Casual Netflix Roald Dahl
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Quick Answer: Henry Sugar is a red pyjamas and striped robe costume where the dressing gown is the one non-negotiable piece.
  • Navy Striped Dressing Gown (essential)
  • Red Pyjama Set (essential)
  • Wine Red Slip-On Loafers
  • Play Money (Sterling Pounds or US Dollars)

Henry teaches himself to see without his eyes so he can cheat casinos out of their money, then gives all of it away to orphanages once the novelty wears off. The dressing gown is the one piece that actually makes this a costume instead of sleepwear, skip it and you’re just a guy in red pyjamas. This is a genuinely niche pick, the film won an Oscar in 2024 but it’s a 39 minute Netflix short, so recognition depends entirely on whether the person you’re talking to happens to have seen it.

Items Total4 Items
DifficultyEasy
VibeWealthy Bored Englishman
Cost$40-$90

Henry Sugar Halloween Costume Items

Henry Sugar Halloween costume infographic showing red pyjama set, navy striped dressing gown, play money, and wine red slip-on loafers

Henry Sugar Costume Items

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Henry Sugar Wes Anderson Roald Dahl
  • 1 Red Pyjama Set (essential)This is the base color that ties the whole look together, and it needs to be a clear red, not maroon or burgundy. Jacket and trousers both, since the collar and cuffs need to show above and below the dressing gown once it’s on.
    See on Amazon
  • 2 Navy Striped Dressing Gown (essential)Without this you’re just a guy in red pyjamas at a party. It needs to be long, ankle length if you can find it, striped, and navy over the red underneath. Those three things aren’t optional, everything else in the build can flex but this piece can’t.
    See on Amazon
  • Play Money, choose oneSterling pounds are character-accurate. US dollars read faster as money to an American crowd. Pick one, not both.
  • 3a Play Money, Sterling PoundsThe character-accurate choice, since Henry gambles at European casinos in the film. Only makes sense if the crowd’s likely to have seen it.
    See on Amazon
  • 3b Play Money, US DollarsReads as money faster to an American crowd who won’t necessarily place the pounds as currency at a glance.
    See on Amazon
  • 4 Wine Red Slip-On LoafersMatch the red of the pyjamas, don’t substitute brown or black. No socks, and slip-on only, nothing that requires bending down to lace up.
    See on Amazon
Henry Sugar outfit reference showing red pyjamas under long navy striped dressing gown with wine red loafers

How to Style the Henry Sugar Costume

The dressing gown is the first thing that registers, and a short or plain robe collapses the whole look into “guy in pyjamas” rather than anyone specific. The red collar and cuffs peeking out above and below the gown do the second most work, if they’re tucked away completely you lose the layered detail that separates this from a random bathrobe costume. At a crowded party the gown might come off from the heat, and the pyjamas alone still read as deliberate rather than half-finished. A tightly knotted belt instead of a loose loop is the detail most likely to make the whole thing look accidental instead of intentional.

He spends three years training himself to see through a deck of cards, walks into a casino, and wins more money in one night than most people see in a decade. Then he gives it all away without much ceremony, like the money was never really the point of any of it.

Don’t knot the belt, loop it

A properly tied belt reads as someone who got dressed on purpose, which is the opposite of the character. Loop it loosely once and let the gown hang slightly open at the chest. It looks like less effort, which is exactly the point.

Fan the money out, don’t fold it into a wallet

A folded bill in a pocket doesn’t register as a prop from more than a few feet away. Hold a visible stack loosely fanned in one hand instead, like you just picked it up off a table and haven’t bothered putting it away. That’s the detail that actually reads as the character rather than just a guy holding cash.

Henry Sugar Group Halloween Costume Ideas

Roald Dahl Universe

Henry Sugar, Willy Wonka & Matilda

Excellent group for anyone who grew up on Dahl, since the three span completely different eras of his writing and none of them need to visually match to be understood together. Wonka’s eccentric colors and Matilda’s plain school uniform sit fine next to Henry’s loungewear, the connection is the author, not the aesthetic.

Henry Sugar Willy Wonka Matilda

Wes Anderson Characters

Henry Sugar, Suzy Bishop, M. Gustave & Sam Shakusky

Strong if the group actually commits to Anderson’s flat, symmetrical style, since that’s what holds four completely different films together rather than any shared story. Anderson fans will clock it fast, everyone else just sees a well-dressed, oddly formal group.

Henry Sugar Suzy Bishop M. Gustave Sam Shakusky

Duo Idea

Henry Sugar & Veruca Salt

Might work, but the connection is thematic more than visual, a man in a dressing gown next to a girl in a fur coat doesn’t read as a pair on sight. It works better as a conversation starter than an instantly recognizable duo, since you’ll likely need to explain that Henry eventually gives his money away and Veruca never learns to.

Henry Sugar Veruca Salt

Men in Robes

Henry Sugar, The Dude & Arthur Dent

Might work, but the three characters have nothing in common beyond all wearing a robe at some point, so this reads as a costume theme rather than a reference anyone gets immediately. It’s a fun premise for a group that already knows all three films, less so for a general crowd.

Henry Sugar The Dude Arthur Dent
Henry Sugar pyjama costume full look with red pyjamas, navy striped dressing gown, and wine red loafers

Henry Sugar Halloween Costume DIY Tips

Building the Look

The dressing gown is the only item worth being picky about. Everything else is closet or basic retail.

  • Dressing gown: buy this one specifically, navy striped and ankle length aren’t easy to find twice.
  • Red pyjamas: check your closet first, any clear red set works.
  • Play money: pick one currency, pounds or dollars, not both.
  • Loafers: wine red specifically, any slip-on works if the exact style isn’t available.

Playing Henry Sugar at the Party

He’s charming, self-interested, and doesn’t perform any of it, he just is that way.

  • Speak in complete, measured sentences. No rushing, no filler.
  • If someone asks what you’re supposed to be, “I taught myself to see without my eyes” is a strong opener.
  • Hold the money loosely, like you forgot you were carrying it.
  • Don’t slouch. The character’s whole posture is someone who’s never had to hurry.

Henry Sugar Halloween Costume: FAQ

Wear a red pyjama set under a long navy striped dressing gown, tied loosely at the waist. Add wine red slip-on loafers with no socks, and carry a fanned stack of play money in one hand.

It’s genuinely niche. The film won an Oscar in 2024, but it’s a 39 minute Netflix short, so most people at a general party won’t recognize the specific character even if the outfit reads as intentional. It works best at a party full of film people or Wes Anderson fans.

Two lines capture him well: “I am very rich, and I have absolutely nothing to do.” and “I practised. Three years. Every day. Then I went to the casino.”

A wealthy, bored Englishman finds a manuscript describing how to see without using his eyes, trains himself in the skill, and uses it to win big at casinos, before giving all the money away to orphanages.

Pounds are more accurate to the character, since he gambles at European casinos in the film. Dollars read faster as money to an American crowd. Pick one, not both.

Benedict Cumberbatch, in Wes Anderson’s 2023 Netflix short film adapted from Roald Dahl’s 1977 story.

Yes, more than most. You’re essentially wearing pyjamas and a robe, no heavy accessories or restrictive fit. The gown can come off if it gets warm and the pyjamas alone still look deliberate.

What skill does Henry Sugar teach himself in the story?

Who plays Henry Sugar in the 2023 film?

What award did the film win in 2024?