Cynthia Rowley and Kit Keenan’s Guide to Building—and Being—a Brand

Fashion designer Cynthia Rowley has built a career on bold moves—and in recent years, so has her daughter, content creator and entrepreneur Kit Keenan. Together, the mother-daughter duo has embraced reinvention as both a necessity and a creative superpower. Rowley’s eponymous fashion brand has weathered major industry shifts. Luckily, Rowley found success in pivoting—with her daughter Keenan who helped bring it into a new era, one TikTok at a time.

As a more famous example, do you remember a little company called Kimono from 2019? Today, it is a billion-dollar brand known as SKIMS. The global shapewear company by Kim Kardashian actually had a fraught beginning full of negative press and accusations of cultural appropriation. But most people don’t remember those early days, proving that even the biggest businesses in the world rebrand sometimes.

“It’s so fun that we get to work together. Our businesses overlap in so many ways,” Keenan says. Rowley laughs, “She comes in and steals clothes all the time.”

On The Dream Bigger Podcast, Rowley and Keenan open up about the power of a pivot—personally and professionally—plus the highs and lows of working in industries that demand constant change, handling online criticism, and how they navigate working together as a family. 

Cynthia Rowley and Kit Keenan: a mother-daughter duo in the fashion world

Cynthia Rowley launched her line in 1988 and built it into a global lifestyle brand offering ready-to-wear items made for adventure. You might also know Rowley from reality TV on shows like America’s Next Top Model and Project Runway. But these days, thanks to Keenan’s online presence, Rowley’s clothes are reaching a whole new generation.

“My social media has helped bring a younger audience,” Keenan says. “That’s also because my mom’s clothes are so cool and can cater to different age groups.”

The collaboration is unofficial—Keenan isn’t technically on her mom’s payroll—but their worlds inevitably collide. Keenan, who grew up watching her mother pull off massive runway shows, has introduced the brand to her own followers simply by living in and having access to it.  

Rowley doesn’t mind: “Literally, people come into my stores and go, ‘This is Kit’s mom’s store. Isn’t that amazing? I feel so lucky. She helps me so much…Kit is just like crushing it.” 

How did Kit Keenan become an influencer?

As an influencer, Keenan has no illusions about the doors her upbringing opened when she entered the content creation space. She garnered fame pretty quickly, having grown up in New York City as the daughter of a fashion icon.

“I attribute so much of my success to my mom,” Keenan says. “Growing up, when people would use the nepo baby term, it was offensive. But at this point in my life, I’m so lucky to have been given the tools and privileges I’ve been given because of my mom. I’ve been able to use her success as an example.” 

That doesn’t mean the path was obvious. “I tried getting into art and investing and film school,” she says. “I have tried on so many hats. Now, I joke that I basically have my dream job because I make little videos all day long. I tried on a bunch of different things until I found something that stuck on me and was my calling.”

Rowley, meanwhile, discovered her passion for early, starting to sew dresses at seven years old. For Keenan, her childhood norm was the runway, so when she began filming TikToks with her mom for fun, her followers organically gravitated toward it.

Creative reinvention and staying relevant in a changing world

Regarding evolution, Keenan says it’s required in social media: “It’s a bit weird if you’re stagnant. You have to be constantly evolving. People are afraid of brand change. But the truth is no one cares as much as you do.”

For the Cynthia Rowley brand, change is inevitable, but knowing your through line is crucial. “It’s important to know your authentic self,” Rowley explains. “Once you have that foundation, it’s even more important to stay curious, be fearless, be experimental, and try things out.”

During the 2008 financial crisis and the pandemic, the Cynthia Rowley brand had to evolve to stay afloat. “I thought I was done…I completely reinvented the company and how we work. That was a moment born out of complete devastation that resulted in huge gains for the company,” Rowley says.

Instead of recoiling, Rowley and her team doubled down and worked harder. They changed how they designed, produced, and delivered clothes—creating in small batches, shipping pieces daily, and doing multiple drops per week.

The pivoting and rebranding worked for Rowley and her brand. This September marks their 101st runway show—a full-blown production in different cities and countries. Fittingly, Keenan has never missed a show, from Australia to China to the Canary Islands.

How routine and confidence shape personal and professional success

Growing up in fashion, you might think Keenan was always super confident. In reality, growing up around models created a false notion that she’d also be 5’10” and a gorgeous model someday. But Keenan says, “One day, I remember thinking I’m like 5’2, and I’m not growing anymore. Other than that, I just remember watching my mom’s confidence and having that instilled in me.”

Instead of focusing outward beauty, Keenan says her confidence comes from accomplishing her goals and showing up for herself: “I’m very regimented about my routines because it helps me with my confidence.”

Tackling online criticism with grace and resilience

Keenan grew up in the 2010s in New York City when there was no such thing as influencers. They were called bloggers. She’s been sharing her life online for years and started seeing profits in her early 20s. Her first partnership was with Puma, and when she received her first $500 check, Keenan felt she had made it. 

Of course, with sharing both her personal and professional life online comes criticism. But Keenan says you learn to live with it and embrace your authentic self—even when it’s not a perfect image. “You become a lot more comfortable showing more of yourself. If you are constantly sharing your life online, there’s no way you’ll always be super polished,” Keenan says.

And that might be the biggest lesson from both Rowley and Keenan: authenticity works, but only if you keep moving forward.