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

ACLU By ACLUSponsored

Over the past four years, we grew accustomed to a regular barrage of blatant, segregationist-style racism from the White House. Donald Trump tweeted that “the Squad," four Democratic Congresswomen who are Black, Latinx, and South Asian, should “go back" to the “corrupt" countries they came from; that same year, he called Elizabeth Warren “Pocahontas," mocking her belief that she might be descended from Native American ancestors.

But as outrageous as the racist comments Trump regularly spewed were, the racially unjust governmental actions his administration took and, in the case of COVID-19, didn't take, impacted millions more — especially Black and Brown people.

To begin to heal and move toward real racial justice, we must address not only the harms of the past four years, but also the harms tracing back to this country's origins. Racism has played an active role in the creation of our systems of education, health care, ownership, and employment, and virtually every other facet of life since this nation's founding.

Our history has shown us that it's not enough to take racist policies off the books if we are going to achieve true justice. Those past policies have structured our society and created deeply-rooted patterns and practices that can only be disrupted and reformed with new policies of similar strength and efficacy. In short, a systemic problem requires a systemic solution. To combat systemic racism, we must pursue systemic equality.

What is Systemic Racism?

A system is a collection of elements that are organized for a common purpose. Racism in America is a system that combines economic, political, and social components. That system specifically disempowers and disenfranchises Black people, while maintaining and expanding implicit and explicit advantages for white people, leading to better opportunities in jobs, education, and housing, and discrimination in the criminal legal system. For example, the country's voting systems empower white voters at the expense of voters of color, resulting in an unequal system of governance in which those communities have little voice and representation, even in policies that directly impact them.

Systemic Equality is a Systemic Solution

In the years ahead, the ACLU will pursue administrative and legislative campaigns targeting the Biden-Harris administration and Congress. We will leverage legal advocacy to dismantle systemic barriers, and will work with our affiliates to change policies nearer to the communities most harmed by these legacies. The goal is to build a nation where every person can achieve their highest potential, unhampered by structural and institutional racism.

To begin, in 2021, we believe the Biden administration and Congress should take the following crucial steps to advance systemic equality:

Voting Rights

The administration must issue an executive order creating a Justice Department lead staff position on voting rights violations in every U.S. Attorney office. We are seeing a flood of unlawful restrictions on voting across the country, and at every level of state and local government. This nationwide problem requires nationwide investigatory and enforcement resources. Even if it requires new training and approval protocols, a new voting rights enforcement program with the participation of all 93 U.S. Attorney offices is the best way to help ensure nationwide enforcement of voting rights laws.

These assistant U.S. attorneys should begin by ensuring that every American in the custody of the Bureau of Prisons who is eligible to vote can vote, and monitor the Census and redistricting process to fight the dilution of voting power in communities of color.

We are also calling on Congress to pass the John Lewis Voting Rights Advancement Act to finally create a fair and equal national voting system, the cause for which John Lewis devoted his life.

Student Debt

Black borrowers pay more than other students for the same degrees, and graduate with an average of $7,400 more in debt than their white peers. In the years following graduation, the debt gap more than triples. Nearly half of Black borrowers will default within 12 years. In other words, for Black Americans, the American dream costs more. Last week, Majority Leader Chuck Schumer and Sen. Elizabeth Warren, along with House Reps. Ayanna Pressley, Maxine Waters, and others, called on President Biden to cancel up to $50,000 in federal student loan debt per borrower.

We couldn't agree more. By forgiving $50,000 of student debt, President Biden can unleash pent up economic potential in Black communities, while relieving them of a burden that forestalls so many hopes and dreams. Black women in particular will benefit from this executive action, as they are proportionately the most indebted group of all Americans.

Postal Banking

In both low and high income majority-Black communities, traditional bank branches are 50 percent more likely to close than in white communities. The result is that nearly 50 percent of Black Americans are unbanked or underbanked, and many pay more than $2,000 in fees associated with subprime financial institutions. Over their lifetime, those fees can add up to as much as two years of annual income for the average Black family.

The U.S. Postal Service can and should meet this crisis by providing competitive, low-cost financial services to help advance economic equality. We call on President Biden to appoint new members to the Postal Board of Governors so that the Post Office can do the work of providing essential services to every American.

Fair Housing

Across the country, millions of people are living in communities of concentrated poverty, including 26 percent of all Black children. The Biden administration should again implement the 2015 Affirmatively Furthering Fair Housing rule, which required localities that receive federal funds for housing to investigate and address barriers to fair housing and patterns or practices that promote bias. In 1980, the average Black person lived in a neighborhood that was 62 percent Black and 31 percent white. By 2010, the average Black person's neighborhood was 48 percent Black and 34 percent white. Reinstating the Obama-era Fair Housing Rule will combat this ongoing segregation and set us on a path to true integration.

Congress should also pass the American Housing and Economic Mobility Act, or a similar measure, to finally redress the legacy of redlining and break down the walls of segregation once and for all.

Broadband Access

To realize broadband's potential to benefit our democracy and connect us to one another, all people in the United States must have equal access and broadband must be made affordable for the most vulnerable. Yet today, 15 percent of American households with school-age children do not have subscriptions to any form of broadband, including one-quarter of Black households (an additional 23 percent of African Americans are “smartphone-only" internet users, meaning they lack traditional home broadband service but do own a smartphone, which is insufficient to attend class, do homework, or apply for a job). The Biden administration, Federal Communications Commission, and Congress must develop and implement plans to increase funding for broadband to expand universal access.

Enhanced, Refundable Child Tax Credits

The United States faces a crisis of child poverty. Seventeen percent of all American children are impoverished — a rate higher than not just peer nations like Canada and the U.K., but Mexico and Russia as well. Currently, more than 50 percent of Black and Latinx children in the U.S. do not qualify for the full benefit, compared to 23 percent of white children, and nearly one in five Black children do not receive any credit at all.

To combat this crisis, President Biden and Congress should enhance the child tax credit and make it fully refundable. If we enhance the child tax credit, we can cut child poverty by 40 percent and instantly lift over 50 percent of Black children out of poverty.


We cannot repair harms that we have not fully diagnosed. We must commit to a thorough examination of the impact of the legacy of chattel slavery on racial inequality today. In 2021, Congress must pass H.R. 40, which would establish a commission to study reparations and make recommendations for Black Americans.

The Long View

For the past century, the ACLU has fought for racial justice in legislatures and in courts, including through several landmark Supreme Court cases. While the court has not always ruled in favor of racial justice, incremental wins throughout history have helped to chip away at different forms of racism such as school segregation ( Brown v. Board), racial bias in the criminal legal system (Powell v. Alabama, i.e. the Scottsboro Boys), and marriage inequality (Loving v. Virginia). While these landmark victories initiated necessary reforms, they were only a starting point.

Systemic racism continues to pervade the lives of Black people through voter suppression, lack of financial services, housing discrimination, and other areas. More than anything, doing this work has taught the ACLU that we must fight on every front in order to overcome our country's legacies of racism. That is what our Systemic Equality agenda is all about.

In the weeks ahead, we will both expand on our views of why these campaigns are crucial to systemic equality and signal the path this country must take. We will also dive into our work to build organizing, advocacy, and legal power in the South — a region with a unique history of racial oppression and violence alongside a rich history of antiracist organizing and advocacy. We are committed to four principles throughout this campaign: reconciliation, access, prosperity, and empowerment. We hope that our actions can meet our ambition to, as Dr. King said, lead this nation to live out the true meaning of its creed.

What you can do:
Take the pledge: Systemic Equality Agenda
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Featured image by Shutterstock

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