3 Ways to Dress Like a Gangsta (2024)

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Last Updated: November 3, 2022

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   Wear baggy wide-legged jeans. Loose-fitting pants that sag around the waist became trendy among urban youths whose belts were confiscated in prison, resulting in a low-slung baggy style among ex-cons and real-life gang members.^[1] When buying jeans, try on multiple sizes to get a fit that's snug enough to stay up, but hangs low on your hips and bunches around your shoes.

   • Try getting pants that hang appropriately without a belt, or try getting oversized pants and cinching them up around your hips with a belt where you want them to rest. Make sure to combine the look with colorful boxers so you're not letting anything inappropriate show.
   • Enterprising clothing manufacturers like Rocawear began making pants designed to be worn with a sag. They make regular blue-denim colors as well as bright reds and pastel colors. Shop around to find colors and play with different styles.
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   Buy some fresh white t-shirts. An iconic "gangsta" style combines baggy jeans and an oversized, extremely clean white T-shirt. Typically you can buy the shirts in packages of 2 or 3, and dispose of them after a couple of uses. The extreme whiteness and cleanness of the t-shirt is very important. You want to look as if they were fresh out of the package.

   • Make sure they're big enough so that the sleeve of the t-shirt covers your elbow. They should be several sizes above what would be considered a normal t-shirt fit.
   • Alternatively, get some tank-top style undershirts of a normal fit. This is also a common "gangsta" style.
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   Rep your teams. It's common to wear local college or professional sports jerseys. Basketball jerseys are probably the most common, but football and hockey jerseys are also popular. Pick jerseys from your favorite players from the teams you like, or go for a throwback jersey for a more vintage look. These are often somewhat expensive, which is part of the attraction: jerseys suggest wealth and regional pride.^[2]

   See Also

   How to Dress up Like a Gangster: 8 Steps (with Pictures) - wikiHow1920s Gangster Fashion: Decoding the Era’s Iconic StyleGangster Party Motto - Ideen, Deko, Outfits, SpieleHow To Dress Like A Gangster (15 Outfits & Style Tips)

   • Regional representation isn't a necessity. Pick a jersey that looks cool. Also, if you're not a sports fan, you can still wear a jersey. The most popular basketball jerseys in the last few years have been LeBron James and Carmelo Anthony, while the most popular football jerseys have been Robert Griffin III and Peyton Manning.
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   Get some kicks. High-top basketball shoes are always a popular choice, for many of the same reasons jerseys are popular, and you'll want them to be as clean as the shirts. Shoes should be fresh and new-looking, as if they just came out of the box. Popular brands include Nike Jordans, K-Swiss, and Timberland work boots.

   • Sometimes, you'll see the shoelaces removed, or reverse-laced with the ends tucked down into the shoe, or tied under the tongue of the shoe, rather than showing on top.
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   Put it all together. Try different combinations of shirts and pants with your shoes to get the most desirable look for what you're going for. The most classic look might be bright white t-shirts with saggy blue jeans and super-crisp K-Swiss shoes. Accessorize to complete your new persona.

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   Wear gold or silver. Necklaces, earrings, watches, bracelets, and rings are all common accessories, as long as they are large, shiny, and gaudy. The goal isn't to wear a small tasteful stone, but to wear a shiny piece of "bling." Wearing a single long gold or silver chain is a classic look. Diamonds or other precious stones are also common. The shinier the better.^[3]

   • It's commonly disputed where the phrase "bling-bling" came from, now that it is a household term. One of the earliest references was in the 1993 Super Cat track "Dolly My Baby."
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   Top it off with a sports hat. Hats should have a flat brim and keep the stickers on (but not the bar code sticker). Follow them same general guidelines for the jersey. Hats can be used to illustrate regional pride. Keep the brim as flat and strait as possible, worn at a jaunty angle for maximum effect.

   • Some people who dress in this style like to keep the stickers on the hat, which--like the t-shirts and shoes--suggests that the hat is brand new, fresh, and signifies wealth.
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   Wear other athletic gear like sweatbands. Sweatbands worn around the wrist, forearm, and head are very popular. Even if you're not playing sports and have no intention of draining some threes later in the afternoon, looking as if you might be able to throw down on the court is a plus. Get sweatbands in black or white and match them to your clothes.

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   Consider a grill. Grills are gold, silver, platinum, or diamond-studded dental casts worn over the top teeth, bottom teeth, or both. Generally, they're removable, but some people have their grill attached permanently. Some can be wildly expensive (Paul Wall's custom grills can cost more than a new car) but some made of cheaper metals can be a few hundred dollars. Wearing a grill suggests extreme wealth, as if you had run out of places to wear jewelry and resorted to the mouth. It's a striking and instantly recognizable look.

   • The grill can trace its roots to 1980s New York, but became more popular in mainstream culture in the mid-2000s when southern rappers popularized it. Lil Wayne is notable for his ubiquitous grill.
   • The long-term dental affects of wearing a grill are unknown. Lil Wayne was forced to receive significant dental work upon entering prison, because his teeth had apparently been wrecked by wearing the grill and not properly cleaning it.

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   Get a fade. Fades require a barber who knows how to do it. Ideally, this short-cropped hair will gradually fade into nothing as it goes down the neck. You'll need to get it touched up fairly often, at least once a week to keep the look. Again, the common theme here is to suggest wealth: you can afford to get your hair cut every week.^[4]

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   Try cornrows. Wearing these tight braids in a variety of patterns is a common and iconic gangsta look. Basketball players and suburbanites alike have embraced this method of braiding tight controlled rows of hair close to the scalp. Worn long or short, the cornrow is a classic look.

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   Wear do-rag. The do-rag originated as a style when African-American men would "conk" their hair in the early 20th century. Conking involved essentially killing the hair with chemicals to straighten out its curls, sometimes resulting in a specifically reddish bleached tint. Malcolm X, for instance, was known as "Detroit Red" as a young man for his usually-conked hair.

   • After the process was completed, which involved a painful process of combing lye into the scalp, the "do" needed to be protected by wearing a "do-rag" around for a couple of days. In this way the rag became popular. Wearing a do-rag generally has no connection to the conk do anymore, though the rag is still common.

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