Rapper Future attends The Biggest Labor Day Takeover at Compound on September 5, 2020 in Atlanta, Georgia; Rapper Meek Mill is seen on June 13, 2018 in New York City; Offset attends the Balenciaga Womenswear Spring/Summer 2023 show as part of Paris Fashion Week.
Source: Prince Williams/Wireimage; MediaPunch/Bauer-Griffin/GC Images; Jacopo M. Raule/Getty Images For Balenciaga

These 2000s Hip-Hop Fashion Trends for Men Are Coming Back Like They Never Left

As the landscape of the hip-hop culture changes, so does fashion — however, these fashion staples from the 2000s will never go out of style.


Jan. 2 2024, Published 9:58 p.m. ET

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Y2K fashion proves that the early 2000s was a wonderful time to be alive.

From the bedazzled name belts to the oversized jeans and shirts, the outfits were iconic (and sometimes trainwrecks.) While there are many trends that we were happy to see fizzle out, the 2000s were a very era, especially for hip-hop.

This leaves us questioning: Which of the biggest trends will make their way back?

Here are the freshest hip-hop fashion staples of the 2000s that are spinning the block right now.


durag edited
Source: Edward Berthelot/Getty Images

Christian Combs at Casablanca during Paris Fashion Week.

This fashion staple started rising in popularity from the late 90s to the early 2000s as icons like 50 Cent and Jay Z made it iconic.

Initially, this scarf barely made it out of the house of those who wore it because it was a garment made to preserve a person’s waves after a haircut. Over the years This piece was worn from the bedroom to basketball courts, making it a true street style piece.

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Allen Iverson made the trend even more popular when he started sporting a durag on the court to keep his braids fresh and add style to his uniform. Rappers even started wearing them to suit and tie events and eventually, the garment made it to the big screen.

This Y2K trend began to slow down once those who did not understand hip-hop culture and trends started associating durags with criminalization and other stereotypes.

However, durags have gotten a major rebrand since then. High fashion even celebrates the, which is clearly here to stay.

Timbaland Boots

timbs edit
Source: Prince Williams/WireImage

Timbaland, Swizz Beatz and Fat Joe onstage during the BET Hip Hop Awards 2023 at Cobb Energy Performing Arts Center on October 3, 2023 in Atlanta, Georgia.

This 2000s wardrobe staple proves to be way more than a pair of boots made for construction workers. Timberland boots will always have a strong connection with hip-hop culture.

Consumer journalist Rob Walker reports in his book, Buying In: "The legend goes that the first 'urban' buyers of Timberland boots were New York drug dealers — guys who had to stand on the street all night and needed the best possible footwear to keep them warm and dry."

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These boots were found on the feet of Tupac, in the lyrics of Biggie, and in the high graces of many others. This 6-inch construction boot is very popular in New York City and is still an iconic fashion trend today.

Bucket Hats

ti wears a bucket hat
Source: Prince Williams/WireImage

T.I. attends Latto's birthday party at The Bank on December 22, 2023 in Atlanta, Georgia

Bucket hats started getting very popular in the 80s when Run-D.M.C. and LL Cool J rocked them on stage.

Though the hat was originally designed to keep water and rain out of the wearer’s eyes, this trend quickly became a popular hip-hop accessory. As the trend became more mainstream, the Kangol bucket took center stage.

As hip-hop history progressed, the trend lived on — for example, Jay Z rocked a bucket in his “Big Pimpin” video.

Regardless of the year, these trends are proof that hip-hop will never go out of style.

The author’s content and opinions have not been pre-reviewed, approved or endorsed by Discover.

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