November 21, 2011 Hip Hop Fashion – 10 Worst Dressed Hip Hop Icons

Hip Hop Fashion – 10 Worst Dressed Hip Hop Icons

Hip Hop fashion has been interlocked with the culture of hip hop since its humble beginnings. As its progressed, the fashion has become more flamboyant, creative, unique and essential to this list, eccentric as hell.

Over the past decade, hip hop fashion has become a billion dollar business that is making artists like Jay Z, 50 Cent, and P Diddy more money than their actual music.

Hip Hop fashion has endured criticism since its inception between the baggy pants, bandanas, pants sagging, and bling, the judgement has perpetuated because of these controversial trends, whether that is deserved or not is irrelevant to the fact that this style of clothing is immersed in our culture.

As you are about to see, the results of trying to be special and stand out in the crowd can be embarrassing. We understand that fashion can only be judged from the eye of the beholder, but don’t tell us that Flava Flav is a revolutionary.

10.Soulja Boy

As a direct result of the internet, Soulja Boy has skyrocketed to mainstream fame for his catchy records and his bizarre fashion. The 17 year old proved that he wasn’t just a one hit wonder. Nevertheless, he has his own tweak on fashion that has earned him considerable attention.

Soulja Boy wearing Fat Joes SweaterThe creator of such classic hip hop material as “Crank That”, “Yahhhh!, and “Soulja Girl”, is always dressed in his flyest gear.

In this picture, you can see that he has borrowed Fat Joe’s sweater. Is it possible that behind them obnoxious glasses hides talent?

Soulja Boy is currently writing a book entitled “Teenage Millionare”, at 19 years old, this is quite an accomplishment.

We might have to back off our criticism of the successful young entrepreneur after he has remained relevant now for three years.

9.Snoop Dogg

Snoop Dogg’s trademark smooth flow, quirky catchphrases, and his natural charisma have kept him at the forefront of raps elite for over a decade. Even if he is not the most lyrical rapper in the history of the game, Snoop Dogg keeps himself relevant by dropping albums and starring in blockbuster hits.

Malice in Wonderland is his tenth solo album, despite sticking to the same formula he has for a while, it has received mostly positive reviews. He probably didn’t touch a pen. When you’re a pimp like Snoop, it’s expected that you will wear some abnormal fashion. Sometimes, he takes it a bit to far though.

Snoop dogg wearing a kiltHe came out wearing this a couple years ago at the MTV Europe Music Awards in Germany.

The skirt is cool, I’m more freaked out by seeing Snoop Dogg wearing a suit.

As I reminisce, what ever happened to the greatness of “Gin n Juice” and “Who Am I (What’s My Name)?”.

We appreciate Snoop Dogg for not caring about anyone’s opinion; still we’re not co-signing on this one.

With his larger than life personality and over the top antics, I doubt he is going to make an exit from the hip hop scene any time in the near future. When his career finally comes to a drum roll; not many will argue the merits of his superstar status.

8. Missy Elliot

She is well known for her theatrical performances and captivating records. Missy Elliot might be known in the same capacity for wearing some obscure fashion.

Even her clothing line “Respect M.E.”, produced by Adidas, has the Missy touch.

Missy Elliot - 2006 VMA's She likes to shock and awe at concerts and for special appearances.

Take, for instance, this well-received performance at the VMA’s in 2006.

When she decided to appear wearing a garbage bag. What else could it be? Honestly.

She has pushed the envelope on fashion before, the multi-platinum artist won’t get our stamp of approval for this outfit.

When you have hit singles with the consistency of Missy Elliot – you’re free to wear what you’d like — who are we to judge?

7. Kriss Kross

They are best known for being a talented duo in the 90’s. These impressive youngsters were set to leave a legacy and did they ever.

They are best known for being a hip hop duo in the early 90’s that wore their clothes backwards. They did have brief moments of success. When they released their first album,”Totally Krossed Out”, the single “Jump” reached the top of the billboard charts.

When they returned to the spotlight in 96. All the magic had completely faded, “Young, Rich – Dangerous”, had a more gangster approach. The fans weren’t buying it – the album bombed and they haven’t dropped new material since.

Kriss Kross - 1991That’s one of the down falls of hip hop fashion. Even the trends that don’t catch on are permanently weaved into the cultures fabric.

Kriss Kross, will forever be remembered for backwards clothing.

It’s funny, we can laugh at them all we want. At the end of the day, they sold more records than any artist in hip hop has in years. How pathetic is that?

Dressed for success failure.

6. Kanye West

Kanye West has blown up on the scene over the past few years. His lyrics can be powerful and ridiculous in the same bar.

Kanye West - Rocking The GlassesIronic, because so can his fashion. He has been praised for his style and creativity both as a rapper and a fashionist.

He has reached hip hop celebrity in an almost unprecedented fashion.

He released the anthem “Stronger” in the Summer of 07. It’s a great song with a lot of meaning and we congratulate him on his versatility.

Associated with the song is some funny eye gear. The problem with this particular choice of glasses is they resemble lawn chairs. With so many cool pairs of shades to choose from — we must ask, why these ones?


You have seen the 5 through 10 worst dressed hip hop icons in the history of hip hop. Who do you think topped this list? Click here to see the top five worst dressed.

Shop hip hop clothing brands like Rocawear, Akademiks, and Nike on illestlyrics.com

This article has been republished from its original date, June 14th, 2008.

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5 thoughts on “Hip Hop Fashion – 10 Worst Dressed Hip Hop Icons

  1. @ both of you. We had a best list and Kanye West was on the list too. When you’re an innovative dresser then its going to be hit or miss. Obviously this article was not meant to be vicious. It was just for something specific that they dressed in.

    Just because you make humor out of something doesn’t mean that you’re hating. If the article said that Missy Elliot is a horrible dresser, she doesn’t know what the heck she is wearing, then I would be sympathetic to your view point.

    Of course. It’s also meant to cause debate like this. Keep stating your opinion.

  2. I dont know why you would put Kanye on this list when he has been one of the best dressing artist in the pass 5 or so years. Even with those glasses, after he wore them in he’s video millions of people started buying thoose glasses and wearing them in public
    -xavwur

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