With over 35 years across fashion, retail, and e-commerce, from Bloomingdale’s to Gap Inc. and Old Navy, she brings a perspective grounded in both experience and evolution.
What originally drew you to the fashion industry?
I’ve always believed fashion is more than clothing, it’s confidence. I started my career at Bloomingdale’s, where I learned that what a woman wears can change how she shows up in the world. That stayed with me. Throughout my journey, from Gap Inc. to leading Boston Proper, it’s been about helping women feel seen, powerful, and unapologetically themselves.
What is one shift or challenge shaping the fashion industry right now that leaders should pay attention to?
The biggest shift is the move from brand-controlled storytelling to customer-earned trust. In a digital-first world, you no longer have the luxury of building context over time, you have to earn relevance instantly. That requires clarity of voice, authenticity, and a deep understanding of your customer. For us, everything starts with our muse, Lana, because if she doesn’t see herself in the brand immediately, you’ve lost her.
Where do you see the most interesting opportunities for technology or AI in fashion?
AI’s greatest opportunity is in closing the gap between inspiration and confidence. It’s not just about efficiency, it’s about helping a woman see how something fits her life, her body, and her style. At Boston Proper, we’re leveraging tools across our ecosystem, from Shopify Plus to Kaviyo to personalize the journey, but the real unlock is using AI to enhance storytelling, not replace it. Technology should make the experience feel more human, not less.
Sheryl Clark, what advice would you give to founders building fashion or fashion-tech companies today?
Start with a point of view the “Why”, not a product. The market is crowded, but very few brands truly stand for something. Know exactly who your customer is, what she aspires to, and how you’re uniquely serving her. And then be disciplined, growth comes from consistency, not constant reinvention. The brands that win are the ones that stay relentlessly focused on their customer while evolving how they reach her.
One book, one leader, and one quote that inspire you.
Book: Who Moved My Cheese?
it’s simple, but it captures a truth we’ve lived at Boston Proper: change isn’t optional, and your ability to adapt determines your future. It’s been a helpful way to align teams as we’ve evolved from a catalog business to a digital-first brand.
Leader: Sara Blakely, she built Spanx by trusting her instinct and challenging convention, which I deeply relate to.
Quote: “Explore the journey.” And at Boston Proper, we live by one idea: “Defy all expectations.”
