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.
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 at some point following a heart-wrenching breakup.
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.
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