90's Fashion: Do You Remember LL Cool J Rolling Up His Pant Leg?

LL Cool J riding a bike in the "Loungin' (Who Do Ya Luv?)" music video

Rap Tees Collection USA

Rap Tees Collection EU / UK

The one pant leg rolled-up has many meanings and associations and in this article, we are going to take a look at these. 

In Hip Hop it’s LL Cool J who has made the strongest connection to this phenomena. Many people during the 90s associated LL with the look, but why exactly did LL roll-up his pant leg? Retro Hip Hop Blog thinks we have the answer and we’re going to share it with you!

As many know LL Cool J is a very physical fellow who likes to work out and keep in tip-top shape. So assuming that the simplest answer is the correct one, we think LL falls into explanation number 1.

What is explanation number 1?

LL Cool J riding a bike in the "Loungin' (Who Do Ya Luv?)" music video - Notice the left pant leg  

Explanation number 1 is known as the “ghetto leg” which is rolling up the leg of your pants solely on the right side. This is done to keep your pants clean while riding a bike by preventing it from touching the chain of the bike or getting stuck between the chain and the front sprocket. But when looking at LL Cool J’s pictures we can see that he doesn’t roll up his right pant leg but he rolls up his left pant leg! Wow! What can this mean? Let’s take a look at explanation number 2!

What is explanation number 2?

Pablo Escobar - i.e. "a real drug dealer"

It’s possibly a drug dealing thing signaling whether you are a buyer or a dealer. A user on MetaFilter, Dr_Octaviu says “Right leg up is buying, left leg up is selling. (or visa-versa, I can never remember....)”. While AmericanAlcoholic on Reddit says “I live in a small town in Missouri and here the white trash kids who are wannabe dealers do this and say its to show they're dealers. No real dealers do this, however.”

What’s explanation number 3?

A wannabe drug dealer

Building off of AmericanAlcoholic’s answer regarding small town wannabe drug-dealers, we might want to look at Hammond Police Department’s article on Street Gang Awareness.
Here the HPD discuss the two main gangs that are prevalent in the Northwest Indiana and Chicagoland area, known as "PEOPLE" and "FOLKS”. These particular gangs follow the LEFT & RIGHT rule. The "PEOPLE" gangs wear their identifiers to the LEFT side of the body. This would include but is not limited to, hats, jewelry, or a rolled-up left pant leg. While the "FOLKS" gangs wear their identifiers to the RIGHT side of the body.

Or it just as simple as Russell Simmons (founder of Def Jam & Phat Farm) says? "I've been rolling up one leg of my pants for 20 years. Baggy jeans were a ghetto thing. Now, everybody's doing it. The ghetto is a box that is no longer closed, because of the music industry."


  • Darren

    I’m old enough(55) to remember when the practice originated in the 70s during the disco era. It meant you were cool. And you only did it when wearing “football socks”.(Striped tube socks). The pant leg would end just above the colored stripes. This practice possibly started as a nod to football players.

  • RaymondA

    Its King Philip le Bel. The cross found at Oak Island belonged to a Templar novitiate

  • RaymondA

    One pant leg rolled up,and a " halter " around the neck is an initiation rite of the Masonic Order derived from the Knights Templar symbolizing their torture and debasement through Philip Lee Bel and Pope Clement V.I don’t belong to any Order,but I’ve read Nesta Websters work.

  • TRuck

    I’ve heard but don’t quote me. The one pant lag means u have the “toolie” on you. Two pant legs means 2 toolies.

  • JAy

    He used to be in a gang

Leave a comment

Please note, comments must be approved before they are published

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

You may also like

View all
Example blog post
Example blog post
Example blog post