INSPIRED BY: A Reader comment on A 2023 WLSC Prelim video, “Wait! Is that the same guy making all those reels on Facebook? He’s smooth.”
Over the last six months, new videos of fashion fantastic from Rich Jackson have been lighting up my social media and showcasing another sliver of the stepper way of life. #dapper #chicagosteppin #Chitownswag #whatido #adultfashionsense #letsgotoworksteppers. This stepper’s love for fashion is an unmistakable part of his identity and has caught my attention for years. From how he dresses on a regular day on the steppers set in Chicago to classic outfit moments on the contest stage, Rich Jackson’s style and look have always left a memorable impression.
It’s not just the fashion looks. It’s his moves on the dancefloor. His creative, smooth-energy Facebook reels are the Friday afternoon hype in the livingthe8count Facebook group to prepare steppers for a stepping weekend. You can’t help but feel his energy. Rich Jackson AKA 007 (Double O Seven), is one of the dapper dons out of Chicago, and I had to catch up with him and find out how his life became so stepper sharp.
Meet Rich Jackson
Rich Jackson started stepping in 2011 and has been stepping for about 12 years. He is still going and is nowhere near finished. Born and raised in Chicago, he had seen and known stepping.
“I did the club thing, and it got old in my early 30s, so I fell back. I started going out to eat and going to plays. I was looking for things to socialize.”
Rich Jackson
When his boss invited him to a stepper class, he decided to go because now he had someone who could go and learn with him. He learned it, and he loved it! It was the best decision I ever made. He started with a guy named Chuck, but he is not at the forefront of the community. I believe he came up with Snoop, Dre, and a few others. He was in the background but smooth as butter, and I loved his dance. He taught me at Sweet Georgia Browns in Country Club Hills.
Competing in the WLSC
Chuck told him one day, “I’d love to work with you. I see you got potential.” He saw something in Rich when he didn’t know how to do anything but a basic right turn. Rich laughs as he remembers that when he started, he could not get out of the lane or cross over the lane. Chuck stuck it out with him and taught him the techniques of the dance, and the rest is history.
When Chuck asked Rich, “Have you ever thought about competing?” it tapped into a nerve. Rich was competitive, and coming in the door green, he knew nothing about contests. “They have contests every year. You can win money,” Chuck told him. Rich said, “Sign me up.” In 2011, six months in from learning to step, Rich was on the World’s Largest Contest Stage in the Beginner’s category. In 2016, he placed second in the New Skool category for the WLSC.
Why are you called 007?
I was given that name by a stepper that has been stepping for years. He was known as Dee Dee in the Old School days – Josiah Burt – but they call him Old School Joe today. I call him Joe. He admired how I dressed. He said, “You remind me of double oh seven the way your suits are cut. You remind me of that clean, classic look and style. You know what, Ima call you 007.” I ran with it.
Define stepper sharp, and what does it mean to you?
When I hear stepper sharp, it has to do with your attitude and the way you carry yourself. It means being in a mature state of mind. Stepper sharp is not all about clothes and is not about one thing. It could be the clothes, the walk, the swag, the attitude, and the confidence when walking into a room. Your attire is put together well, your outfit is matching to a tee, and it fits you to a tee. It’s a whole thing. People think it is just about putting on a suit. You can put on a suit that doesn’t fit you right. If you don’t wear it well, that’s not stepper sharp. It’s more than one thing. It’s a laidback thing – not being cocky or arrogant. Chicago brings many things that not many cities can pull off. Chicago is known for “that thing” regarding stepper sharp.
When did you develop your fashion sense?
I think when I hit high school, I found my fashion sense. It was preppy, then. I came up with House Music. Argyle socks and polo shirts for a preppy, clean look. We had style back then. I had penny loafers with Levis. One might say that “ivory look” and it took off from there. When I was younger, my mother used to put me in fashion shows. I don’t know if that had much to do with my loving fashion and knowing how to put clothes together, but I just picked up and ran with it. I’ve been a dresser since high school with suits and ties.
I can dress down just as well as I dress up. I have had a lot of practice, but I try to be conservative. When I dress, I don’t like to be gaudy and overbearing – like, whoa, that’s a lot! I am not saying it doesn’t work for others, but that’s not me. I like to keep it clean. If I put on a suit, it won’t be too much with five rings that say, “Hey, look at me!” It’s going to be just enough, and I keep it a clean and classic look. If I can’t wear it in a business atmosphere, I am not wearing it. I might go ahead and add some colors now and then, but the suit is still cut. I might go out on the edge a little bit, but not too far. This is how I do.
What influences or inspires your fashion?
The 1930s look inspires how I put my attire together. It’s all about the classic look, and it’s got to fit me from head to toe. I like to set trends instead of following trends. I might try something new here or something new there, but it won’t be crazy. It’s going to be doable. Someone might see that and say, “Hey, that’s nice. I wanna try that.” Some of the things that I do are signatures of mine. I picked up a lot of styles from different players in the game and the magazines I have read. When I was young, GQ was the magazine to watch for fashion. I watch videos on YouTube and fashion shows. I watch those things and pick up ideas.
What are some signatures of your look?
The pointed bow tie. I am notorious for that. And the creased pocket square.
You have to wear it. And wear it well. You have to own what you wear. Some people can pull it off, and some can’t. I am not taking anything from anyone. Some people are dressers, and some people just like dressing down. I try to do both – go casual and dress up. Some cats out here are known to wear a suit all the time. I don’t want to be like that. I try to keep a good balance and still be clean-cut, even if it is casual.
At the 50 one day, someone saw me in shorts and said,” You look like you’re about to go golf.” You will hardly ever see me in a T-shirt. If you see me in a T-shirt, I am up to something. I am either about to compete or change clothes for something. Or it is a part of my outfit.
What fashion traditions in the stepping culture do you love?
I love it when we dress up as a culture, and everybody is dressed up. With the pandemic, we fell back from that, but we’re trying to get back to it. I love dressing up, putting on a suit, going out on the town, the shoes, the tie, the cufflinks, the watches, and the smell good. This is a beautiful thing to me. It is about being an adult. This community is an adult atmosphere and arena. We have our ups and downs, but when we come out as adults and play the part and look like adults, it’s beautiful.
I went to the Grand Ballroom at a Good Times Productions set. I walked up, and there was another stepper there, and we were talking and laughing.
The security with the metal detector said, “I just love how y’all do y’all thing.” He had to be in his mid-20s. “You have a good time.”
I said, “Yes, we were young, just like you, but now this is how we get down.”
He couldn’t believe that he saw us dressed up and everything was peaceful. Two black men together and having a good conversation on sight. I told him, “You’ll love this when you get up here and start mingling with your peers on an older level.”
It was a proud moment to hear him say that he saw us like this and that he, a young person, saw something positive in adults.
What it is and what it was
I love to see us dress up and have a good time. That inspires me. Everybody wants to put their character out there. We all want to do that. Some of us have closets of clothes and shoes and want the opportunity to wear them. I respect this culture. When you see me, it goes deeper than the dance. It is about the dance, but it is more to me. I grew up in the streets of Chicago. I have seen the steppers and what it was like. What you see now is sweet, and the cats who I saw weren’t like that. My mother would not let me hang out and go outside and do stuff like that. It was a whole other atmosphere and different types of people. I respected it.
It wasn’t what it is now, but they were all clean as a whistle – with finger waves, Cadillacs with diamonds in the back, the Gators, lizards, snake skins, tailor-made suits, the perm, and the butter. They were just cool and mellow. Coming up and watching that, I respect it. Coming into stepping, I still respect that; what I saw is what I do today. I saw them clean, and so that’s how I get down. Sneaking into parties like the Hummingbird when I was fifteen years old, I saw Jannice and a few other people but did not know who they were. It was different.
How do you choose your outfit for the contest stage, and what is important to consider?
I dress. My partner is first up. I go to her first. I ask her, “How are you feeling? What do you like? What color do you like? And I go from there. I let her choose the colors, and I go from there. Women know what you like and what makes you feel good. So that is first, in my world, the partner has to feel good, and I’ll work around her. When I choose a color, it has a lot to do with what my partner likes. I think that should be with everybody. To me, she is more important when it comes to that because you want your partner to be comfortable. The male can always compliment the female and do that in various ways.
Why is impeccable fashion such a big part of who you are?
Because I represent me. And in my presentation, I want to put an impression on you that I don’t want you to think anything differently. Presentation is everything when it comes to me. How you present yourself is everything; everything else falls into place. I like to stay well put together. It’s being an adult – a seasoned man and some of these things happen. When we were younger, we didn’t know how our pants or jackets should fit, and then as we got older, we learned how to dress and what to put with what. Sometimes, it becomes a habit, and dressing now is a habit for me.
Stepping represents Black culture
We must represent our culture, and stepping is definitely a black thing. That is one thing that we own, and we have to represent it well at all times. We cannot afford to not represent well something that has grown so big in the nation. It’s in different countries now. We must represent it and let them know this is what it is. It’s a mental thing. It’s a swag that Chicago owns, and it’s been like that since I can remember. They have been doing this before me. It’s a whole vibe regarding Chicago Stepping, and impeccable dressing has much to do with it.
Where Stepping Fashion Influence started
If you want to see it, go to a Pimps Ball. Much respect for those guys because they started something huge. I saw it with my own eyes. You’ll see a sprinkle of it when you go to sets, the old timers – the people who were there for real. Much respect for them. I don’t knock the hustle or the game. Get it how you live. They didn’t come outside any other way. They were always in order. I represent what I witnessed.
Super Fly is Super Fly
When my father took me to see Super Fly, I have been messed up ever since. If you want to see where this comes from, watch that movie. The mindset he puts you in, you can feel the pain. I think Super Fly is the coolest dude in the world. I watch it again and say, “I’m stuck.” Cool. Swag. Confident. He was strictly business, the swag, the attire, and no-nonsense. I got a kick out of that.
I try to live like that, but I’m not jumping over fences or coming down the elevator with kilos. Everything about the movie I admire. The game was fierce, and I loved that. When I was young, people watched karate movies and came out doing karate moves. I watched Supa Fly, and I came out pimping. I wanted an El Dorado with lights and a pretty female in the back. That was me!
Rich, what inspired you to start doing the reels?
I am Chicago
I was inspired by the representation of Chicago – number 1. Chicago is on my mind when I do my reels. It is to represent our culture and community, our swag. It has to do with my journey in the stepping arena from when I started to the pain, learning this, learning that. I want to have a record of my journey. This is what I see. My mood. This is how I feel when I am going to a party. When I put things together, how do I keep it 007 – clean and classic? I vibe at the start of the video. When we get a certain mood, we get it. You might put the shoes on, bust a move, and say, “Yeah, these are the shoes I am going to wear tonight!”
Stepper Sharp is more than Fashion
Putting clothes together and putting clothes on. It’s about attitude, confidence, swag. I represent Chicago to the fullest when I put them together to the music. I try to choose music. Josiah told me, “Rich, it ain’t about the music there is a certain flavor to it. It carries that vibe the stepping community demands, and that drives a steppers crowd – it could be new or old music. I try to pick the right music, keep it clean, and keep out the profanity (to keep it tasteful so you can enjoy it). This is what we do and how we do it! Come out and have some fun with us.
Making a positive impact
I have touched young and old people. My daughter at work said someone showed her one of my videos, and she said, “Yeah! That’s my Dad.” That made me feel good.
I get questions about the bowties I have made, where I got my shoes from, or where I can find that suit, and can you show me that footwork you did.
It’s a positive thing for the community. I wouldn’t be doing it if I didn’t know how to step. It’s respect for the dance and the community. I don’t want you to get confused that this dance is lame or for old people. We’re just grown folks, and this is what we do.
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Welcome! I am the writer Sonji Stewart. These are my travel stories about my Chicago Stepping experiences, traveling from city to city to dance. I hope my stories encourage you to join me in the adventure.
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Rich Jackson
This is a Beautiful thing! Thank you so much! 🔥 💯