What started as a bad breakup led Kendall Reynolds, founder and design director of her namesake brand Kendall Miles, to create a luxury footwear brand worn by the likes of Rihanna and Kehlani. Reynolds’ path to entrepreneurship embodies the glow-up that we all experience (or at least hope to) at some point following a heart-wrenching breakup. Reynolds’ story of entrepreneurship, Black girl magic, and luxury fashion has resonated with the accessory-obsessed not just for the relatable come-up story, but because her brand stands out amongst luxury competitors with her commitment to “glorifying the importance of being the best, wanting the best, and doing the most.”
Hailing from the South Side of Chicago — Hyde Park to be specific — Reynolds didn’t originally set out to be a luxury shoe designer. “I actually thought that I was going to go into finance. In high school and college, I was interning at investment banking companies. I thought I was going to go into a Wall Street type of business,” Reynolds tells Teen Vogue over Zoom. “I followed my high school boyfriend to Los Angeles, where I attended USC,” but following the breakup, she pivoted to her creative comeback. “I made the conscious decision to just channel all of that heartbroken, depressed, and negative energy into something creative.”
Reynolds explains that her shoe game actually blossomed before Kendall Miles took root. Her interest was piqued in the same place many young fashionistas begin their love affair with style: their mother’s wardrobe. “My mom was such a shoe girl,” she says, “I would always play in her closet. I'm a size bigger than her so I would squeeze my feet into her Manolo Blahniks and her Louboutins.” But Reynolds’ mother saw the potential for the brand from the beginning. Once the budding designer started distancing herself from a career in finance, she began dipping her toes into the creative outlet that would take her to designing luxury shoes. She began with a few drawing classes here and there, a few intro Italian language classes, and eventually landed in a shoe design program in Milan at Arsutoria. With her mother’s blessing and financial backing, and her pre-existing business track, she focused her senior year at USC on getting her business off the ground and into the hands of shoe lovers everywhere.
“Everyone’s asking ‘Where are you going to go work, what jobs are you applying for?’ I just couldn't see myself going to work for somebody at that time. I was so hell-bent on doing my own thing, building my own lane, and finding my own path,” Reynolds explains of her journey starting her business in college. “Here we are nine years later. And during that time you're seeing your friends get married and have families. You're seeing your friends get raises and get promoted,” but her choice to follow a different path also brought some doubts along the way, questioning if she should have been following that same structure.
“When you have a startup, you live and breathe your business, you wake up thinking about your business, and you go to sleep thinking about your business. And so you question yourself, ‘Am I on the right path? Is this work really paying off? Will my brand ever be successful?’ But you have to really be focused on your goals and give yourself grace.”
In just nine years, she went from starting as “a 21-year-old Black girl making shoes in Italy,” to building a Black women-owned and operated business that rivals some of the biggest luxury shoe brands. The designer is whole-heartedly dedicated to creating a brand by and for women, which is more unique than you’d think. According to the Fashion Minorty Alliance, only 14% of the luxury brand creative directors are women, and only 1% are from minority backgrounds. However, Black women make up 30% of the total sales in the luxury sector. The designer explains that even though Black women are big spenders in the luxury space (not to mention the trendsetters) there’s a lack of loyalty to any one luxury brand because “no one luxury fashion house is communicating to us in an authentic way.” So in terms of how Kendall Miles is reaching their customers, Reynolds states “It's not performative. It's not opportunistic. It's very authentic. We can talk to the girls like they're our homegirls.”
The intentionality of listening to her customers’ needs is evident in every single design. “The footwear industry is still very male-dominated. A lot of women's needs are getting left on the table all for the aesthetic look by the male gaze,” she explains of what sets Kendall Miles apart from other luxury shoe brands.
Reynolds refuses to sacrifice comfort for style. The designer shares how she had to consider biology alongside aesthetics in the design process, applying knowledge of demographic differences to better cater to customers whose feet didn’t fit the traditional European luxury market. “What I found [in our market research] is that Black women and Jewish women in America have some of the widest feet and the most footwear struggles.” So Reynolds' hack to creating a more comfortable wearing experience is simple: “Manufacturing shoes that are made for people like us, and consider our proportions in the manufacturing part of the process.”
The designer owns the fact that her college breakup led to the birth of her creative comeback. “Definitely my villain origin story. It gave all the revenge,” she tells Teen Vogue. She explains how this was a defining moment not just for her personally, but for her future and career. But make no mistake, Kendall Miles is so much more than a glow-up story of finding your footing post-breakup. “A business making no money is a hobby,” she professes.
Since the brand’s launch in 2016, their showstopping heels have been worn by the likes of Kehlani (in the sold-out bone-toned Pout boots), Taraji P. Henson (in the mink Throne pumps) on the season finale of Empire, Fantasia Barrino on The Color Purple press tour, Ashanti (in the red snakeskin Michelle pumps and the oxblood Attitude boots), and the ultimate style icon Rihanna herself — and that’s just the tip of the celebrity placements. “We’ve got to get Beyoncé in some shoes. That's on our mood board.”
Could a Texan-inspired cowboy boot be next on the horizon, à la Beyoncé’s upcoming album direction? Reynolds urges “Manifest it with us."
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