How to Dress up Like a Gangster

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Whether you are getting ready for Halloween or are planning on attending a themed party, this article will teach you how to get your gangster on!

Method 1
Method 1 of 2:

Dressing Like an Old-Fashioned Gangster

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  1. Gangsters in the 20s and 30s dressed up rather elegantly. A typical outfit included an all-black, gray, or pinstriped suit with a tie. Keep the color scheme simple; stick to black, white, gray or brown.
    • If you don't have a suit jacket, then wear a vest and roll up the sleeves of your collared shirt.
    • Either wear a white collared shirt with a black tie or a black collared shirt with a white tie.
    • Wear a pair of black or brown dress shoes.
    • If you want to add a dash of color, just try to make them work in harmony. Use the color wheel and look at which colors sit together on it. For example, blue and green work really great together.
  2. Find a black, white, gray, or pinstripe fedora. A popular look among traditional mobsters was to wear a black hat with white trim, or white hat with gray trim.
    • Be sure that the hat matches your suit. Again, stick with neutral colors like black, white, gray, and brown.
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  3. Toy guns can be purchased from Halloween stores or toy stores. Consider buying a squirt gun and spray-painting it black.
  4. In old films, criminals, gangsters, and other "bad guys" were often portrayed smoking cigars. While you certainly don't have to smoke it, carrying a cigar around will add an authentic element to your costume.
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Method 2
Method 2 of 2:

Dressing Like a Modern-Day Gangster

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  1. Unlike their old-fashioned counterparts, modern-day gangsters wear baggy, casual clothes that come in various colors.
    • Find a pair of baggy jeans in either blue or black. You really can't go wrong with jeans, but trainers have also been making a comeback of lately.
    • Buy an oversized t-shirt. [1] A plain white shirt can also work.
    • Wear an oversized hoodie, a puffy jacket or a large sweatshirt. [2]
  2. Gangsters are notorious for their tattoos. You can draw on fake tattoos using a pen, or apply temporary stick-on tattoos.
    • Many gang members get tattoos of the faces of loved ones who have passed away on their upper arms.
    • Draw tattoos on your face, neck, and/or chest.
  3. Find long silver or gold chains with dollar signs, crosses, or other symbols on them. Try wearing multiple chains of different lengths and colors.
  4. Either tie a bandana around your head or wrap it around your neck and tie it in the back. Beanies can be worn in any color but should not have any designs or logos on them.
    • A cap can also work, being worn in different combinations or styles. [3]
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  • Question
    Can I keep brass knuckles with me when acting like a gangster?
    Community Answer
    You can, but in some places brass knuckles are illegal, so be aware of your local laws.
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    Not Helpful 22 Helpful 63
  • Question
    Can I use a fake gun for a modern gangster, too?
    Community Answer
    Yes, some modern gangsters (especially street gangsters) carry guns.
    Thanks! We're glad this was helpful.
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  • Question
    Can I wear sunglasses to look like a gangster?
    Community Answer
    Yes, many gangsters wear sunglasses to look fly on the streets. Just get some baggy clothes and some bling, and maybe a fake tattoo and you'll be good to go.
    Thanks! We're glad this was helpful.
    Thank you for your feedback.
    If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
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      Tips

      Tips from our Readers

      The advice in this section is based on the lived experiences of wikiHow readers like you. If you have a helpful tip you’d like to share on wikiHow, please submit it in the field below.
      • If you live in an area with real gangs, dressing like the wrong gang can get you into a lot of trouble, and you could potentially get hurt. Be wary of what you wear depending on what neighborhood you're in.
      • If you carry a fake gun, people could assume it's real and get afraid and call the police.
      • A lot of gangsters wear bandanas on their heads.
      • Try wearing a snapback cap instead of a beanie.
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      Warnings

      • Remember that some gangs have identifying colors or bandanas. To stay out of trouble, avoid dressing up like a member of a particular gang, especially in neighborhoods or cities where you know these gangs reside.
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        Helpful 8 Not Helpful 2
      • If you decide to take a fake gun, check laws in your area about modifying toy guns. Keep or paint the tip neon orange to help law enforcement know it is a toy and remember to use common sense. Pretending it is real could cause you to get shot or arrested.
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      References

      1. ↑ https://lifestylebyps.com/blogs/mens-fashion-blog/a-beginners-guide-to-dressing-like-a-gangster-rapper
      2. ↑ https://lifestylebyps.com/blogs/mens-fashion-blog/a-beginners-guide-to-dressing-like-a-gangster-rapper
      3. ↑ https://lifestylebyps.com/blogs/mens-fashion-blog/a-beginners-guide-to-dressing-like-a-gangster-rapper

      About This Article

      Article Summary X

      If you want to dress up like an old-fashioned gangster, you’ll need to go for an elegant look. Put on a black, grey, or pin-striped dress suit. Stick to simple colors, such as a white shirt and black tie, or black shirt and white tie. You should also wear dressy brown or black shoes. If you want to dress up as a modern gangster, your outfit will be much more casual. Put on an oversized pair of jeans and a baggy t-shirt in any color you like. You can also add a hoodie or puffy jacket to your outfit. Make your outfit stand out with gold or silver chains with symbols, like dollar signs or crosses. Remember to wear a bandana or beanie to complete your look. For tips on how to accessorize an old-fashioned gangster outfit, read on!

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