1920s Gangster - How to Dress Like Bootlegger Al Capone

Famous 1920s Gangster Al Capone

1920s gangsters were men who controlled the illegal distribution of alcohol during the Prohibition. Just like neighborhood gangs today, 1920s gangster 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. Today TV series like Boardwalk Empire and Peaky Blinders capture this violent time in history.

The 1920s gangster costume can be summed up as men in dark suit jackets (often striped, never black) with matching vests and pants, white or black band fedora hat, contrasting tie, and a cigar in mouth. Most respectable men avoided this look in the 1920s; however, by the 1940s the Zoot Suit was inspired by the “Era of Gangsters.” Because they are similar, men’s fashions of the 1920s and 1940s are often mixed up. “1920s zoot suits” did not exist although the style took roots in the very late 20s among jazz musicians and entertainers.

1920s Gangster Costume

1920s Gangster Look – Black homburg hat, dark grey striped suit, two tone shoes, leather gloves and a walking cane (or is it a weapon?)

Suit- Single or double breasted striped gangster suit jacket with wide lapels. Jackets buttoned up high and fitted well in the early ’20s and were a bit looser by the end of the decade. The fabric was commonly dark grey and white chalk stripe wool. Chalk stripes are wider than pin stripes. Brown stripes, plaid or tweed may have been worn for casual day meetings and by lesser ranking bootleggers. Learn more about men’s suits here.

Pants of the 1920s were mostly high-waisted (at or above belly button) with flat fronts until the late 20 when pleats were introduced. Pants were straight through the leg and cuffed at the bottom with a crease down the center. They fit narrow in the early ’20s and very wide by the end of the decade.

A matching 6 button vest with notch lapels was worn with each suit. Poor gangsters or working class men may not have been able to afford a three-piece suit. They may have worn a suit without a vest or a vest and pants but no suit jacket. A suit jacket, pants and vest were made of the same material. Buy 1920s style men’s suits, pants and vests.

Shirts

Gangster Shirt– A basic button down dress shirt with white collar. Choose a striped shirt for the most authentic ’20s 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 1920s men’s shirts.

Gangster Overcoat– A dark and ominous gangster spends a lot of time checking up on his hidden whisky stills. To stay warm 1920s, men wore a heavy wool overcoat over their suits. They were quite long and plain with simple notch lapels and a one or two button closure. In heavy winter conditions, they were lined in fur. For your look, black, grey or dark brown long wool overcoat will be easy to find.

Men’s Hats

Gangster Hat- While most men of the 1920s preferred wearing bowler 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. Another option is the black homburg, also worn in the 1940s and 1950s by the Godfather.

In summer, the hat of choice for wealthy men, including gangsters like Al Capone, was the straw 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.

1920s Gangster Accessories

Club Collar, Paisley Tie, Collar Pin

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. Shop 1920s style men’s ties.

Suspenders– Suspenders were less of a fashion statement as a necessity to hold up one’s pants. If you wear a vest than suspenders are unnecessary to be fashionable. If you are wearing a shirt without a vest than 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. Buy 1920s style leather or striped suspenders.

Two tone Shoes

Gangster Shoes– Brown and white/tan spectator shoes are the most iconic of the 1920s. Plain black or brown wingtip dress shoes would be a second choice and better for darker suits. For a formal occasion, you can wear black dress shoes with white spats. Gangsters loved to wear spats! Buy 1920s men’s shoes.

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 dangles 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.

Cane– Many wealthy men choose to walk with a gold handled cane.

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.

Need help with your 1920s gangster / mobster / mafia costume? Just ask.