1920s Gangster / Al Capone Suit

The 1920’s Gangster’s were men who controlled the illegal distribution of alcohol during the Prohibition of the 1920’s. Just like neighborhood gangs today, Gangsters mobs controlled certain sections of larger cities. Their territorial battles often ended in blood baths like that of Al Capone’s Valentine’s Day Massacre. The Gangster look can be summed up as men in dark suit jackets, white fedora hat, contrasting tie, and cigar in mouth. Most respectable men avoided this look in the 1920’s however by the 1940’s the Zoot Suit was inspired by the “Era of Gangsters.” To assemble your own 1920’s gangster look you will need the following items:

1920's vintage modern style ganster suitSuit– Single or double breasted pinstriped suit jacket with narrow lapels. Jacket buttons high and is fitted. Fabric was commonly black and grey chalk stripe wool. Brown stripes or tweed may have been worn for casual day meetings. Pants of the 1920’s were mostly high wasted (at or above belly button) with flat fronts.  Pants were straight through the leg and cuffed at the bottom with a crease down the center. Suit jacket, pants and vest were made of the same material. Buy 1920s style men’s suits here. 

Shirt- A basic button down dress shirt with white collar. Choose a striped shirt for the most 20’s look. Get a french or double cuff shirt if you want to wear some snazzy cuff links as well. Read more about and shop for 1920’s Mens shirts.

1920's al capone ganster hat

Hat- While most men of the 1920’s preferred wearing felt Panama hats the Gangster’s hat of choice was the fedora. Hats were either white or black with a contrasting band about 4 inches tall wrapped around the base. With the distinctive front pinch and wide, floppy and pliable rim, the Fedora will unmistakably set you apart from ordinary “gentlemen” of the day. In summer the hat of choice for wealthy men, including gangsters like Al Capone, was the Optimo Panama. Capone owned several Panama hats and even imported a hat maker from Ecuador just to make them for him. For that extra gangster flair wear your hat slightly tilted to the left. Read more about  and shop for 1920s style men’s hats.


Gatsby gold tie

Gold Tie

Tie– Your ties should starkly contrast with your shirt color. A white shirt would need a dark colored tie while a white a gray shirt would call for a white tie. Wide striped ties or small pattern ties in jewel tones were very common among trendy dressers. Gangsters would never be caught wearing a bow tie. Learn more about 1920s mens ties. 

vintage mens wardrobeSuspenders– Suspenders were less of a fashion statement as a necessity to hold up one’s pants. If you wear a vest then suspenders are unnecessary to be fashionable. If you are wearing a shirt without a vest then the suspenders should match the shirt and suit. Black or gray are the most useful. However if you are wearing a white tie, then matching white suspenders against a dark shirt would be most striking.

Pocket Square– Also known as a handkerchief, the pocket square should coordinate with one color in your tie but not necessarily be the exact same material.  Place it  folded in you left heart pocket.

Watch chain with watch. Chain dangle across the vest from watch pocket to clip.  No vest? You can pace you pocket watch in your pants pocket and attached the chain to your belt loop.

1940's men's shoes

Shoes- Black and white spectator shoes are the most appealing. Plain black wingtip dress shoes would be a second choice. For a formal occasion you can wear black dress shoes with white spats.  Gangsters loved to wear spats! Buy 1920’s mens shoes.

Cigar– Gangsters always have a cigar in hand and a shot of “bootleg” whiskey in a flask by their side.

Facial Hair- While most men, including gangsters, were clean shaven a simple, thin, straight mustache was a signature piece for some Gangsters.

Find many of these items and more over at the 1920’s Men’s Clothing page.


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About Debbie Sessions

Debbie Sessions is passionate about wearing history through fashion. She and her husband, Oscar, have turned their hobby into a career by teaching others how to re-create vintage style with affordable new vintage inspired clothing and accessories. We connect shoppers to the best vintage inspired clothing, shoes and accessories and teach fashion history as it was worn by everyday people. Need more help? Contact us anytime.