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 Sweater
The 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?

5. Will Smith
Before he was one of the biggest movie actors in the world. He was just a hip hop rapper, one who happened to wear some unique clothing.
Lil Kim - Wearing NothingMost visibly demonstrated on “Fresh Prince Of Bel Air”, the hit 90′s Television Sitcom, Will Smith had a gigantic wardrobe of innovative hip hop fashion.
He also represented his interesting sense of fashion throughout the 80′s and 90′s in music videos, touring, and promotion.

In those days, hip hop fashion was already eccentric, but Will Smith redefined its eccentricity with a whole series of outlandish outfits that only Will could pull off.
Now, he is one of the sharpest dressed hip hop artists. Will Smith still puts out hip hop albums every couple years when he is not interviewing the president or acting in a blockbuster movie.

4. Lil Kim
She has been extremely successful throughout her music career, ironically as provocative as her lyrics are, Lil Kim’s fashion has greatly exacerbated her already controversial personality.
Lil Kim - Wearing NothingAfter a rough couple years, she is getting back to business, releasing the Mixtape entitled “Ms. G.O.A.T.”.
We’re going to jump back to 2001 and the video music awards. When Lil Kim brought her new style of wearing a bra to the forefront of a live MTV audience.
Can you imagine the shock on everybody’s face when she is wearing basically nothing on her chest?
It’s one thing to be risky and it’s another to wear a flower on your breast. Mystery can be sexy as well, if she wants to get naked – get naked, for playboy.
She has shocked since her debut, and we don’t expect differently from the grammy award winning — electrifying female MC — that has signified what it is be a women in this business for well over a decade.

3. Andre 3000
Andre 3000 has made an impact on hip hop. He is one of the most gifted emcees and his creativity is off the wall. Andre 3000 has no boundaries in his music or fashion.
Andre wearing a BlanketHis duo Outkast with rapper “Big Boi” is one of the most successful rap duo’s in the history of hip hop.
Actually, it wouldn’t be to controversial of a statement, if I said they are the most successful with all respect to Eric B and Rakim.
When it comes to his clothes, he is hit or miss. Maybe even more misses than hits.
When you wear a blanket instead of pants, it’s just getting a bit too ludicrous and you can’t sum it to simple individualism.
He launched “Benjamin Bixby” clothing line with his own perspective on fashion. Hopefully, he’ll tone it down considerably for the masses.
He only deserves the three spot because at least once a year, he wears an outfit that makes you go “Damn” that’s impressive.

2. MC Hammer
If you’re a teenager, you don’t understand how big of deal MC Hammer was in the late 80′s and early 90′s.
Mc HammerHe created monster hits like “U Can’t Touch This” and is one of the top selling hip hop artist of all time.
MC Hammer broke down all kinds of barriers that were holding hip hop back from reaching its current mainstream acceptance, for example being the first rapper to get a big endorsement deal.
Basically, he is responsible for the astronomical figures that hip hop artists are making today.
None of which changes the fact that this rapper started some awful hip hop clothing trends.
Including parachute pants, which are some of the most embarrassing hip hop clothes to ever be made.

1. Flava Flav
Although he wasn’t notoriously known for his bad style during the Public Enemy days. The pioneering group is forever linked with hip hop. Despite the legacy, Flava Flav, has went onto new challenges.
Flava Flav Can't DressFlava Flav, decided that, he wanted to be a part of one of the most absurd reality shows in TV history. The agenda was simple to have a group of girls compete over the love of Flava Flav.
“Flavor of love” has become a great success and I’m sure his lack of fashion sense has contributed greatly to the ratings.
Flava Flav comes bursting into number one with his signature Viking Helmet on his head, a grill, and his flamboyant shirt.
I don’t think it would be a stretch to say that Flava Flav will dress like this until he dies. I don’t know about you, but I’m not going to lose any sleep over it.

We could try to stop this madness or maybe, just maybe, we need to accept that hip hop fashion is always going to push the boundaries of what is good and what is not and somewhere in the middle is what makes this type of fashion so irresistible.

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