Meet Sally Gupta

We had the good fortune of connecting with Sally Gupta and we’ve shared our conversation below.

Hi Sally, can you walk us through the thought-process of starting your business?
The idea for ChicBySally came from a deeply personal place. As a tech leader, mom, and lifelong fashion lover, I found myself—and many women around me—slowly losing touch with our personal style as life got busier. Between motherhood, demanding careers, and daily responsibilities, it’s easy for women, especially over 30, to stop prioritizing themselves. But I truly believe that feeling good in what you wear can reignite confidence and self-worth.

I’ve always had a deep love for technology—not just as a career, but as a powerful tool for innovation and creativity. With ChicBySally, I saw an opportunity to merge that passion with fashion by using AI to reimagine how style can be discovered and expressed. I created a curated, digital fashion gallery that blends timeless chic with a modern, tech-driven twist.

Through AI-generated fashion, I design and showcase looks that are aspirational yet relatable, freeing style from seasonal trends or store shelves. My goal is to help women rediscover their love for fashion, feel empowered in their skin, and see that elegance and strength can go hand in hand—no matter what phase of life they’re in.

It’s more than just fashion to me—it’s a movement to bring joy, creativity, and confidence back into the lives of women who do it all.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
My career has been a journey of evolution—from software developer to tech leader to fashion curator. What sets me apart is the way I’ve blended two worlds that are rarely paired together: technology and fashion. I’ve spent years leading cloud architecture teams and building digital solutions, but I’ve also always had a deep love for fashion and storytelling. Launching ChicBySally was my way of uniting these passions.

Getting to this point wasn’t easy. As a woman in tech, I’ve faced my share of challenges—biases, burnout, and the constant pressure to prove myself. Add motherhood to that equation, and it becomes a delicate balancing act. But each challenge taught me resilience, focus, and the importance of staying connected to my “why.”

What I’m most proud of is staying true to myself—using technology not just to build systems, but to build beauty, expression, and impact. I want the world to know that ChicBySally isn’t just about pretty outfits. It’s a platform that redefines what it means to be stylish, powerful, and seen—especially for women navigating the beautiful chaos of life.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
If my best friend were visiting, I’d plan a week that blends charm, Texas flair, and relaxed elegance.

We’d start with a stroll through the beautiful Adriatica Village in McKinney—a hidden gem with European vibes, perfect for boutique shopping and waterside dining. For that true Texas experience, we’d head to the Stockyards for the rodeo and longhorn cattle drive—it never fails to impress.

A day at Grandscape in The Colony would be a must for open-air shopping and a stop at the Windmills restaurant—great views, great food, and a relaxing vibe. And of course, we’d wrap it all up with authentic Texas BBQ at Dickey’s Barbecue Pit—because no trip to Texas is complete without it!

Who else deserves some credit and recognition?
When I think about the people who’ve inspired and supported me on my journey, one name stands out: Leeanne Hackney. Leeanne is not only an accomplished realtor in the Dallas-Fort Worth area but also a devoted mom who exemplifies the art of balancing a thriving career with family life. ​

Her ability to serve her clients with passion and integrity while raising four children is nothing short of inspiring. Leeanne’s dedication to her profession and her family mirrors the very essence of what I aim to celebrate with ChicBySally.​

ChicBySally was born out of a desire to empower women—especially those juggling multiple roles—to rediscover their personal style and confidence. Witnessing Leeanne’s journey reinforced my belief that it’s possible to pursue one’s passions without compromising on personal commitments.​

Leeanne’s story is a testament to the strength and resilience of women who do it all. Her example continues to inspire me and countless others to strive for balance, pursue our dreams, and support one another along the way.

Website: http://chicbysally.org

Instagram: https://www.instagram.com/chicbysally

Youtube: https://www.youtube.com/@ChicBySally

Other: https://shopmy.us/savvyfashionista