Things You'll Need
Colorful button-down dress shirt
Holster or garter for holding your gun
Black patent leather dress shoes
Fishnet or seamed stockings
How to Dress Up Like a Gangster. They didn't call it the Roaring 20's for nothing. Gangsters knew how to dress, but more importantly, they knew how to have fun. Whether you need a Halloween costume or you're throwing your very own 1920's themed party, a gangster costume is perfect for any man or woman who wants to have a good time and look dangerous while doing it.
Don a pinstriped suit. Pick a suit that is black or dark gray with white or light gray stripes. Make sure it fits impeccably, as looking good is vital to a real gangster. Dress in a suit with a tight pencil skirt, instead of pants, if you're a woman.
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Wear a button-down dress shirt under your suit. Choose a brightly colored silk or cotton shirt, in black or purple. Wear a solid-colored tie made of a high sheen silk or cotton, for a cool, gangster touch. Women can wear a flapper's dress with lots of bangles.
Slick your hair back, if you're a man, with gel or pomade to give it a slick shine. Women should pin their hair pack, or wear it down with sexy finger waves. Stylish headbands and skullcaps, both often beaded, were also popular with women during the 1920's. Keep makeup simple and sultry, with bright red lipstick and dark eyeliner.
Wear a white or black fedora that matches your suit. Either of these hats are acceptable, but make sure they're made of felt, if you want to be taken seriously as a gangster.
Carry a toy gun. Pistols or a Tommy gun will work; genuine 1920's gangsters carried both. Carry your handgun in a shoulder holster. If you're a woman, buy a garter instead of a holster to hold your pistol.
Wear patent black leather wingtips or oxfords if you're a man, and black pumps if you're a woman. Women should also pull on a pair of fishnet or seamed silk stockings for an authentic gangster's moll look.
Complete your look with a silk handkerchief in your breast pocket and a gold watch. A pocket watch with a chain is the most authentic choice. Women should wear big diamond jewelry. Costume watches and jewelry will work just fine.
1920's gangsters transported alcohol during the Prohibition. Carry a flask to complete your look.