How Kesha McLeod Went from Working In Retail to Styling The Biggest Names In Sports

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The truth about purpose is that sometimes you have to let it find you.

It doesn't follow a strict timeline, and the aha moment often hits you when you least expect it—maybe...

in your teens or your early twenties, just in time for you to decide which career path to pursue and what jobs to send your resume to. It may lie dormant while you move and shake within your industry, building up a Rolodex of clients that will make the average person do a double take.

Or in the case of celebrity stylist Kesha McLeod, it might not hit you until long after you've built a respectable career, and are looking for the next part of your legacy.

“I'm figuring out my purpose and my values and my core values," says McLeod. “But [in the meantime] I can speak on [it] to a younger generation that wants to do what I want to do."

Photo Credit: Majorie Preval

We're ducked off of the streets of Melrose in a minimalistic store for high-end streetwear brand, Daniel Patrick, where McLeod is teaching me “How to Build a Bomb Wardrobe: 101." First lesson—start with the basics. White tees, colored shirts, denim jeans, these wardrobe essentials are how a good foundation is built. She skips past monocolored clothing displays and flicks through a rack of brightly colored options, pulling out a long yellow shirt that would be a dress on me but fits perfectly for one of her many athletic clients. Chris Bosh, maybe? Serena Williams? James Harden? Andre Iguodala? She's a little tight-lipped on the details, but there's a guarantee that the threads will end up on any one of those style icons.

“I usually talk to them in the beginning of the season since it's athletes predominantly," she says. “We talk about where we're going and how we're styling them, what we're going to work with, what are their inspirations, and things like that."

For McLeod, style has always been innate. The Jamaican-Trinidadian was seemingly born with the ability to piece good looks together, a skillset that faired well for her in her various retail positions where she started from the bottom, only to be promoted to supervisor within a few weeks.

“Styling, to me, is basically psychological and it's common sense within. I just bring the person that's inside out."

Around the age of 19, shortly after receiving her associate's and prior to her pursuing a fashion marketing degree, she worked a dead-end job as a telemarketer for just a month before spotting a H&M ad that led her to walk out the door on her lunch break.

“I don't mention it because it's not significant, but if you think about it, it is because if I would've never opened that paper, bored out of my mind, I would've never taken this route."

Working in the H&M showroom was enough to open her mind to the possibilities of styling as a career, and gave her a vision for her life. She didn't just want to be in the retail stores, she wanted her work to appear on the red carpets, on the backs of athletes and entertainers. Taking initiative, she researched out to companies that aligned with her goals and found work at a boutique agency before transitioning over her talents to work with notable stylist Rachel Johnson, founder and CEO of the Thomas Faison Agency.

“I wanted to be bigger and better and she was the biggest in her field, especially in sports. So I went and worked with her for seven years and then I went out on my own."

James Harden | Photo Credit: Kesha McLeod


Not something new to McLeod, and definitely something that has been a staple throughout her career. Branching out on her own was one of her best mistakes. At the time it seemed crazy, stupid even—it meant that she had no guarantee of income, no steady clientele, no big name to back her, and no comfortable cushion to catch her if she fell.

“How am I going to pay my rent? How many more roommates am I going to have? Do I move back to my grandmother's house?

Do I get a steady job, because a lot of people do that in this industry, and now you're freelancing at a retail store, or you're bartending? And there's nothing wrong with that until you it figure out, but it could be hard to balance because then you get discouraged a lot. You're the one to push through to get yourself there, and it's a lot of self-care and meditating; it's a lot of figuring it out and I've reached a lot of dead ends in the beginning, and still to this day."

Andre Iguodala | Photo Credit: Matt Edge

Of course, she landed on her feet.

She tapped into the relationships that she built over the course of her career, many of which came during her three-year hiatus from the agency she worked at when she went into styling for music artists such as Rick Ross, Young Jeezy and Jadakiss, and that spread through word-of-mouth to everyone from athletes to CEOs to politicians.

“For you to think and get dressed is a whole other part of your brain that you've got to use, that's why Steve Jobs always wore the same thing," she explains when I asked about the latter of her clients. “It's a part of your brain that you have to use to get dressed—it's a lot when you have to focus 100% on the game or the company that you're building or even yourself or what you're doing, it's a lot to get dressed."

For McLeod, styling is a form of storytelling. One of her biggest client's, Chris Bosh, is a carefully crafted narrative written through style. Yes, he can rock a good suit, but he's also constantly evolving—even the books that he reads hints at a shift in his mindset, and it's McLeod's job to make that reflective in his style.

“You basically start chapters with all of your clients to try and finish a book, and you tell these stories through these garments and through these different threads."

Her own style, she tells me, is a story of growth and confidence. Today, she's rocking black Topshop jeans, a cutoff Yeezus t-shirt, and a blunt bob-cut that screams, “I'm bold and I'm confident," which ironically wasn't always the case.

Photo Credit: Kesha McLeod

“It's not always one thing when you're not confident. It always stems from somewhere else," she says. “You can be unconfident about the way you look, so now you're afraid to do certain things and you think you're going to always fail. And you're going to fail because that's the mindset you're putting into it. "

"You have to always think with the right mindset, and now you dress better, you look better, your skin is glowing, you're happier, and everybody wants to be around you. Now your career is booming and you're a great person, and positive will attract positive."

As with any true master of their craft, evolvement never stops, and neither does teaching.

While McLeod crosses accomplishments off her list of 2017 goals, including getting placement in Forbes and Vogue, she now finds herself at a point where she can begin passing the baton to the next generation of stylists through workshops and panels, and use her gift and her platform for something beyond herself and her clients.

“It doesn't have to be anything super prolific. What we're doing now can change somebody else's life. I can speak to a younger generation that wants to do what I want to do, but one day I'm going to transition out, so I'm at a crossroads right now trying to figure out where I'm taking styling and where I'm taking me as a brand, my career, and where I'm going to be bigger and better in the next five years."

Perhaps that's a part of her purpose. Not just dressing celebrities in fancy threads, but also inspiring others to fearlessly go after their dreams—and to do so with strength, poise, and authenticity.

“[Styling] is my gift and my talent and it's what I want to do, but it doesn't define who I am. You don't ever want something that you do to define who you are; you always want to still be true to yourself."

Kesha McLeod's 3 Tips for Dressing Like a Celebrity

Organize Your Closet Before Spring Cleaning. “If you start purging with a messy eye, you're going to throw away something that you could've used that you could apply later on. So you've got to clean it up and go from there."

Find Your Staple Item. “I have this black tweed jacket that I got from H&M in Paris in 2005 that I would never get rid of. It's crazy looking but it's me and I can't get rid of it."

Load Up the Accessories! “Every little detail makes sense—every chain. Now it's two chains. And then it's all of these little details that make the outfit what it is."

Featured image courtesy of Kesha McLeod

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