1920s costume tips
Planning to host A Speakeasy Murder?
An easy way to make your murder mystery party feel like a genuine 1920s Chicago speakeasy is to encourage everyone to dress the part. The good news is that you don’t need elaborate costumes or historically perfect outfits.
A smart suit, a vintage-style dress and a handful of well-chosen accessories are often all it takes to capture the glamour and excitement of the Roaring Twenties.
Whether you’re playing a powerful gangster, a glamorous jazz singer, a sharp-dressed politician or an elegant socialite, these costume ideas will help every guest look at home in your speakeasy.
Most outfits can be put together from clothes you already own, with inexpensive accessories such as hats, pearls, braces or feathered headbands adding the finishing touch.
Suggestions not rules
Treat these suggestions as inspiration rather than strict rules; after all, every character deserves their own unique style.
Plus, see here for photos and stories from A Speakeasy Murder parties.
The cast of A Speakeasy Murder
The Management
Fat Stan Belluccio
As the owner of the speakeasy, Fat Stan is one of the most influential men in Chicago’s underworld. His clothes should immediately convey wealth, authority and confidence. Think expensive tailoring rather than flashy excess—the sort of outfit that tells everyone he’s in charge before he says a word.
- Dark pinstripe or double-breasted suit
- Fedora
- Crisp white shirt and bold tie
- Pocket square
Polished shoes or spats - Gold watch chain or signet ring
- Cigar (prop)
Florence
Florence is far more than simply the boss’s wife. She’s intelligent, organised and clearly involved in running the establishment, dressing with understated elegance rather than theatrical glamour. She should look like someone who belongs in the finest hotels as much as an underground speakeasy.
- Smart tailored dress or skirt suit
- Cloche hat (optional)
- Long pearl necklace
- Gloves
- Structured handbag
- Tasteful jewellery
Jimmy “The Weasel” Smith
Stan’s trusted lieutenant is almost as sharply dressed as his boss, but lacks quite the same air of effortless authority. His clothes are immaculate and practical, suggesting someone who always expects business—and occasionally trouble.
- Dark suit
- Fedora
- Waistcoat
- Tie with tie pin
- Pocket watch
- Leather gloves tucked into a pocket
Alicia “Angel-Face” O’Riley
Florence’s younger sister enjoys fashionable clothes and isn’t afraid to stand out. Her style is sophisticated and feminine, with just a little extra glamour compared with Florence’s more businesslike appearance.
- Chic satin or silk dress
- Faux fur stole
- Cloche hat or feathered headband
- Long gloves
- Elegant jewellery
Tommy “The Horse” Davies
One of Stan’s trusted cronies, Tommy has the look of a man who can handle himself if things turn unpleasant. His clothes are smart enough to fit into high society, but there’s a practical edge beneath the polished appearance.
- Dark suit with waistcoat
- Fedora
- Tie slightly loosened
- Heavy overcoat
- Leather gloves
- Large ring or chunky watch
The Staff
Pickles
Pickles is the person who keeps the speakeasy running behind the scenes. Forever carrying drinks, moving furniture or solving problems, they should look practical, busy and ready for anything.
- Shirt or blouse with rolled-up sleeves
- Waistcoat (optional)
- Apron
- Flat cap (optional)
- Braces (optional)
- Smart trousers or a simple skirt
- Tea towel tucked into a pocket or belt
Tony
Every great speakeasy needs a professional bartender. Tony should look smart, efficient and perfectly at home behind the bar, mixing cocktails throughout the evening.
- White or striped shirt
- Black waistcoat
- Bow tie
- Sleeve garters (optional)
- Smart black trousers
- Polished shoes
Sammy Snake-Eyes
The head croupier is calm, disciplined and impossible to read across the poker table. A crisp, formal appearance helps reinforce the cool professionalism expected from someone running the gambling room.
- White shirt or blouse
- Black waistcoat
- Green or black visor
- Bow tie or neat necktie
- Sleeve garters (optional)
- Smart black trousers or long dark skirt
- Pocket notebook or score pad
Al
The pianist provides the soundtrack to the evening and dresses comfortably enough to perform for hours. His look is relaxed compared with the rest of the staff, but still unmistakably 1920s.
- White shirt with sleeves rolled up
- Waistcoat
- Simple tie or bow tie
- Flat cap (optional)
- Slightly worn smart shoes
Sasha White
The double bass player is effortlessly cool. Always wearing dark glasses, Sasha has the unmistakable look of a seasoned jazz musician.
- Black shirt, blouse or roll-neck
- Black trousers or long dark skirt
Black waistcoat or jacket - Dark sunglasses
- Fedora or cloche hat (optional)
Bobby White
Playing alongside Sasha, Bobby has a similar stylish look. Together they should look like members of the same jazz band without appearing identical.
- Black shirt or blouse
- Black trousers or skirt
- Waistcoat or smart jacket
- Smart shoes
- Dark sunglasses (optional)
Lola
As the star attraction, Lola should immediately command attention whenever she enters the room. Sparkle, elegance and confidence are the order of the day.
- Sparkling evening gown
- Long gloves
- Feather boa or faux fur stole
- Statement jewellery
- Glamorous hairstyle
Mitzy
One of the dancing girls, Mitzy embraces the youthful energy of the Roaring Twenties. Fringe, movement and bold accessories all suit her perfectly.
- Short fringed flapper dress
- Feathered headband
- Long beads
- Dance shoes
- Bright lipstick
Tillie
Tillie performs alongside Mitzy, so coordinating colours or styles creates a convincing chorus line. Matching accessories can look particularly effective.
- Flapper dress
- Long beads
- Feathered headband
- Gloves
Phyllis
Like the other dancers, Phyllis should look lively, glamorous and ready for the dance floor. Matching the other performers helps create a striking visual effect.
- Flapper dress
- Long necklace
- Hair ornament
- Gloves
The Clientele
Officer Pilkington
Officer Pilkington is a policeman—but not a particularly honest one. His clothes should suggest someone whose uniform standards have slipped along with his morals.
- Rumpled grey or brown suit
- Police badge
- Fedora
- Slightly crooked tie
- Well-worn shoes
- Trench coat (optional)
Velma Du Bois
A notorious socialite, Velma knows exactly how to make an entrance. She should look effortlessly glamorous, with luxurious accessories that announce her wealth before she even speaks.
- Elegant black flapper or cocktail dress
- Long pearls
- Fur stole
- Long gloves
- Beaded handbag
- Statement jewellery
Alfonso “Linguini” Marino
Linguini is another powerful gangster who enjoys displaying his success. Unlike Stan’s understated authority, Linguini isn’t afraid to be a little more flamboyant.
- Immaculate pinstripe suit
- Fedora
- Bright silk tie
- Pocket square
- Gold jewellery
- Cigar (prop)
Sugar Sands
As a famous singer, Sugar embraces the glamour of the entertainment world. She should look every inch the celebrity.
- Sequinned evening gown
- Long gloves
- Faux fur stole
- Sparkling jewellery
- Feathered hair accessory
Benny “Ankles” Johnson
Linguini’s right-hand man dresses well but avoids overshadowing his boss. He should look capable, loyal and quietly stylish.
- Smart dark suit
- Fedora
- Waistcoat
- Polished shoes
- Pocket square
Mayor Trelawney
The Mayor is a respectable public figure and dresses accordingly. Conservative tailoring and immaculate presentation suit the role perfectly.
- Conservative dark suit
- Fedora or homburg
- Neat tie
- Pocket watch
- Smart overcoat (optional)
Kit James
The Mayor’s secretary is neat, organised and always prepared. Practicality is just as important as appearance.
- Smart shirt or blouse
- Waistcoat, cardigan or tailored jacket
- Smart trousers or a neat skirt
- Notebook or folder
- Polished shoes
Sofia Meers
Sophisticated without being flashy, Sofia follows the latest fashions while remaining tasteful and elegant.
- Stylish day dress
- Cloche hat
- Long necklace
- Smart handbag
- Gloves
Trilby Madison
A fashionable writer researching Stan’s life, Trilby balances style with practicality. Trilby looks ready to interview someone at a moment’s notice.
- Tailored jacket or cardigan
- Smart shirt, blouse or dress
- Smart trousers, skirt or tailored dress
- Cloche hat or fedora (optional)
- Notebook and fountain pen
Laurie Evans
Trilby’s co-writer shares a similar sense of fashion but with a slightly more artistic flair. Practical clothing mixed with fashionable touches works well.
- Smart tailored outfit
- Shirt or blouse
- Long scarf (optional)
- Smart shoes
- Notebook
- Spectacles (optional)
Oswald Murphy
Hollywood producer Oswald Murphy has never been accused of blending into the background. His bold clothes are designed to attract attention wherever he goes.
- Eye-catching checked or light-coloured suit
- Cravat or flamboyant tie
- Fedora
- Pocket square
- Walking cane
- Flashy jewellery
Ava Monroe
A silent film star should radiate old Hollywood glamour. Luxurious fabrics and sparkling accessories suit her perfectly.
- Elegant evening gown
- Faux fur stole
- Long gloves
- Statement jewellery
- Glamorous make-up
J. D. Oakey
Oswald’s personal assistant is efficient, dependable and meticulously organised. A neat professional outfit complements the role.
- Smart shirt or blouse
- Tailored jacket or waistcoat
- Smart trousers or skirt
- Notebook or clipboard
- Pens
- Polished shoes
Sly Swanson
A charming gambler with a reputation for luck, Sly dresses with a little more personality than the average guest. Bright colours and stylish accessories help reinforce his confidence.
- Stylish lounge suit
- Bright waistcoat
- Colourful tie
- Fedora
- Pocket square
- Pocket watch
- Playing cards peeking from a pocket (optional)
Reno Edwards
A newcomer eager to fit into Chicago’s fashionable social scene, Reno dresses well without appearing quite as extravagant as some of the regular clientele.
- Fashionable daywear
- Smart jacket or cardigan
- Trousers, skirt or tailored dress
- Gloves (optional)
- Stylish hat
- Small handbag or pocket watch
Roxy MacDougall
As the wealthy owner of a department store, Roxy naturally wears the latest fashions. Whether in a sharp suit or an elegant dress, the overall impression should be one of confidence, prosperity and impeccable taste.
- High-quality tailored suit or fashionable dress
- Stylish hat
- Long gloves (optional)
- Statement brooch, tie pin or jewellery
- Quality leather handbag or pocket watch
- Polished shoes
Lady Patricia Fortescue-Smythe
Lady Patricia is an ageing English aristocrat whose wardrobe belongs to an earlier era. Surrounded by fashionable Americans embracing the Jazz Age, she clings proudly to the elegance of Edwardian high society, making her stand out wherever she goes.
- Full-length Edwardian-style gown
- Large hat (optional)
- Pearls or heirloom jewellery
- Fur stole
- Gloves
- Walking cane or ornate handbag
A lorgnette or opera glasses make the perfect finishing touch.
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