When it comes to dressing the part for a 1920s murder mystery party, the devil’s in the details—and in the pinstripes. Whether you’re playing the part of a smooth-talking mob boss, a jazz-club crooner, or a private eye who always gets his guy (and his gin), nothing sets the scene quite like authentic Roaring Twenties style.

Let’s break down what makes men’s 1920s fashion such a standout—and why the best mystery parties come with wardrobe (and entertainment) built in.

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Pinstripes, Fedoras, and the Power Suit of the Speakeasy

The cornerstone of a great 1920s gangster costume? The suit. Think double-breasted, wide lapels, bold pinstripes, and maybe even a pocket square for that extra pop of class. Back in the day, the suit was more than just a fashion statement—it was a power move.

Pair that with a fedora, slicked-back hair, suspenders, and two-tone Oxfords, and you’ve got a look that says, I came to solve crimes… or commit one. Even just a vest feels classy while being non-restrictive, allowing you to wine, dine, and mingle with ease. The newsboy cap is always a great alternative if the trilby hat isn’t quite your style.

You also don’t have to rob a bank in order to afford this classic look either. Thrifting a suit has never been easier with plenty of options from Goodwill to mom-and-pop vintage shops offering style at a low price. Maybe even grandpa has something in his closet from his heyday he can dust off for you.

Ideas for a mobster look:

• Pinstripe or plain suit jacket
• Black or blue overcoat
• Vest or waistcoat
• White button-down shirt
• Oxford shoes
• Fedora, trilby, or newsboy cap
• Trousers with suspenders

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Dressing for the Mystery: Not All Heroes Wear Capes, But Trench Coats Are Cool Too

Not everyone’s the mobster. Maybe you’re the detective in a classic Prohibition-era style trench coat, with a low-brimmed hat and a tie that screams “I take bribes, but only the classy kind.” Or maybe you’re the jazz lounge regular in a vest, bowtie, and rolled-up sleeves, nursing an old fashioned and a secret or two. Costume shops or Amazon offer detective badges and magnifying glasses that will make certain no one questions your authority.

Ideas for a detective look:

• Brown trenchcoat
• White button-down shirt
• Brown trousers with suspenders
• Brown brogue or ankle boots
• Badge
• Brown fedora

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From Gatsby to Gangland: Easy Ways to Look the Part

The beauty of the Roaring Twenties attire is that it walks the line between glamorous and dangerous. Think Great Gatsby meets Boardwalk Empire—everyone looks good, but someone’s getting whacked before dessert. If you’ve got a little extra cash burning in your pocket (and desire to look sharp), hop over to Historical Emporium to peruse their high-quality, ’20s-authentic costumes.

Accessories can really make the look, so why not experiment with pocket watches, pipes, or walking canes? A monocle isn’t just for the Monopoly guy, you know!

Ideas for a bartender look:

• Black vest or waistcoat
• Pinstripe button-down shirt
• Sleeve garter/armband
• Cocktail shaker
• Black trousers
• Black dress shoes

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Why a DIY Party Is the Real Crime

Have you ever tried herding twelve people into character roles while also cooking dinner and writing a believable murder plot? It’s enough to make even the most dapper gangster break a sweat.

Leave the detective work to the guests and the party-planning to the professionals. The Murder Mystery Company doesn’t just bring the plot—they bring the pizzazz. You just dress up, show up, and enjoy the kind of immersive entertainment that would make Gatsby jealous.

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Ready to Step Into the Mystery?

Whether you’re hosting at home or booking a show at a venue, The Murder Mystery Company is the easiest way to bring a vintage caper to life—no acting skills (or sewing machine) required.

For help planning a truly unforgettable, killer evening, call 888-643-2583 or fill out one of the contact forms right here on the page. Trust us: with the costumes, characters, and chaos already covered, all you’ll need to do is solve the crime… or cover it up.