Behind Kendall Miles’ Success: The CEO & Designer Talks Mentors, Inclusion and Strategic Growth

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Kendall Reynolds, CEO and designer of her luxury shoe brand Kendall Miles, has been building her business for nearly 10 years. And the entrepreneur has come a long way from launching the brand during her senior year of college in 2015 until now.

She said, “I’m so proud of myself for remaining a luxury brand, made in Italy, through language barriers, increasingly expensive costs, and pushing for larger, wider, more inclusive sizing for women of all different ethnicity. It is no easy feat staying in business for 9 years as a young founder, I am immensely proud and grateful.”

She’s had help along the way, noting mentors including Jamie Wynn, president of Jimmy Choo North Americas, who is currently advising Reynolds on her product assortment expansion plans and retail strategy.

“A great mentor sees where you are currently, understands where you want to grow to and helps you establish a roadmap. In that process they can give you access to resources, put you in rooms, invest in you,” said Reynolds, adding that Wynn has emphasized product diversity.

Kendall Miles first launched as brand focused on high heels offered in luxurious materials, colors and embellishments. As a Black designer, she emphasized that Black women have built her business. “Point blank period,” she said. Now, Reynolds’ goal is to take the brand further and create an offering that appeals to a wider audience with more wearable shoes.

As I’m continuing to get older, as the business is continuing to get more mature, I want to have products that appeal to other demographics of women, too. That’s super important to me. And you notice, different women have different preferences when it comes to style,” she explained. “I’ve never envisioned going towards kitten heels or loafers, or low-heeled boots. And even ballet flat, but you can’t just have a super niche product. I want to be a designer that really hears my customer and really can also deliver on what they want and need.”

Reynold’s first started growing her business via trunk shows across the country where she has been able to create a loyal customer-based that continues to shop with her. Those events have since evolved and she continues to host try-on parties in key markets in the U.S., including Austin, Texas, and Little Rock, Ark., for example. In addition to that, she is focusing on direct-to-consumer by scaling the brand’s website. In terms of wholesale, Reynolds is looking to keep that succinct and partner with retailers that can take the brand further while simultaneously complementing her DTC business.

But building a brand hasn’t come without challenges. “There are very distinct highs and lows,” she said. “When the drop for the season doesn’t perform in a way that feels like growth for the brand, it’s hard. When momentum dies down after a successful period, it’s hard. I bounce back by taking the slow periods to strategize on a big comeback by harnessing a new vision.”

Most recently, Reynolds has reintroduced a returning style with her latest collection: Delicate Desires. It includes the brand’s Halo silhouette in three new colorways — crisp white matte, smooth red nappa, and textured black calf leather. The sandal also features a wide-foot friendly toe-box, minimalist toe strap, and side bumpers for stability and comfort, a Swarovski crystal chain with a suspended ringlet that allows the chain to be removed, and a 4-inch stiletto.

kendall miles, shoes
Kendall Miles Halo Sandals

The offering, according to Reynolds, captures the essence of the eternal struggle between light and darkness, with each shoe retailing at $475.

To coincide with the shoe release, Kendall Miles is also introducing the Halo bag, available in red and white, which retails for $1195.

kendall miles, shoes
Kendall Miles Halo bag and heels.

A version of this article appeared in the June 3 print issue of FN, as part of the “Women Who Rock” special section. On June 5, FN and Two Ten Footwear Foundation honored these women at a live event in New York City.

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