Then and Now: The Evolution of Pimpin’


Nothing to wear to your next “Pimp n’ Ho” Ball?  Well, read on for both historical and contemporary inspirations for your ensemble.

Back in the day, to be described as a ‘pimp’ was a negative as it strictly referred to shady types who manipulated young ladies into working for them as prostitutes.  Pimps were thought of as having Svengali-type personalities with over the top wardrobes: larger than life archetypes that most of us only ever encounter in movies.

The ‘original’ pimp look can be attributed to Chicago mob boss Al Capone.  Having made his millions in the illegal booze trade and prostitution rings, according to Wikipedia, Capone had the habit of “interviewing” new prostitutes for his club himself.

More than 60 years after his death, today Capone is still the most famous mobster. He managed to make his mark on both law enforcement and in the style department.

Al Capone poster

Take notes, guys.  It’s the fedora, suit (pinstripe NOT optional), crisp white shirt, matching tie,  handkerchief, lapel flower, shiny dress shoes, topped it all off with an expensive cigar.  This is basic Pimp Look 101.

Fast forward to the 70’s when the movie genre blaxploitation emerged and flourished. These budget flicks inspired satires and comedies that ironically established the ‘pimp’ character more firmly and in a more positive and rather humorous light.

And how did movie pimps compare to real life ones? From Al Capone, it all came down to Iceberg Slim.

Iceberg Slim Pimp book

Iceberg Slim was a real-life pimp and an intelligent one at that, having been measured with an I.Q of 175. He started pimping in Chicago after dropping out from Tuskegee Institute in 1937.

Stylewise, Slim kept a sharp but more casual fashion profile than Scarface (Capone was the original Scarface). Slim replaced the crisp shirt with a turtleneck and the suit with a stylish overcoat.  The umbrella prop instead of a cigar and used as a cane -which in the future will be transformed into what we know as a ‘Pimp Stick’.  And the shoes… still shiny, but do pay attention to the heels.  You probably know where we’re going there, and you’re absolutely right.  It’s the beginning of the famous (or infamous for some) goldfish heels made popular by the movie “I’m Gonna Git You Sucka”.

Pimp Shoe

Before we get into the guy who’s most known for wearing that, here’s another real-life pimp who’s living lifestyle in his all day every day.  He’s Archbishop Don “Magic” Juan, who used to be a pimp but is now known mostly for his music, entertainment and congregation.

Archbishop Don Magic Juan

Yes, the Archbishop ushered in the modern pimp style.  So the Archbishop have might quit the pimpin’ game and turned to God, but he still embraces the look.  A true pimp has somewhat of a royal air about him, and here’s Don “Magic” Juan at his regal best, pimp cup in hand:

Don Magic Juan - CD cover

The Pimp cup somehow became the must-have accessory for this look, next to the diamond-studded jewelry and fur coats.

Back to the notorious goldfish heels, it’s from the 1988 movie titled “I’m Gonna Git You Sucka”.  It’s actually an exaggerated version of the 70’s platform shoes which was hugely popular among men and women, and the man who’s known best from wearing it is Antonio Fargas for his role, Flyguy. The seventies might not be much in jewelry, but BIG is the keyword.  The hats are big, the lapels are gigantic , the colors are loud and the bellbottoms look like the bells of Notre Dame.


As time passes by, Fargas toned down the yellow and the zebra and got rid of the goldfish heels, but to take down the attitude? Never.  Here he is at the 2004 premiere of the remake of “Starsky and Hutch”, where he also made the character “Huggy Bear” famous, decades ago.

Antonio Fargas

The hats can get wider, the clothes can get bigger, but a true pimp stays consistent with his style.  Blues singer who’s also known as  “The West Coast Godfather of the Game” or “The Pope of Pimping”, Fillmore Slim, stays true to the old-skool pimp look:

Fillmore Slim

Fedora with normal fedora lid check, classic black suit check. No tie, but jazz up the sharp black shirt with gold patterns and don’t forget the diamond-studded dollar sign ring and a thick pinkie ring to cap the whole look.

Have you decided which pimp era you like?  Or do you feel like mixing things up?


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