November 21, 2011 Hip Hop Fashion – 10 Worst Dressed Hip Hop Icons – 2

Hip Hop Fashion – 10 Worst Dressed Hip Hop Icons – 2


You have seen the worst dressed hip hop icons with their wack styles. Who do you think made the 5-10 worst dressed list? Click here to find out who made 5 through 10.

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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