Executive Wardrobe Styling: Dressing With Confidence in Leadership

One of my long-time clients is a CTO at a Fortune 500 company based in Atlanta. She is highly intelligent, personable, and well-respected in her organization. Despite her seniority, she came to me with a clear goal: she wanted her wardrobe to better reflect who she is today.

She needed to strike a thoughtful balance—approachable yet authoritative, age-appropriate yet current. In her early 50s, she also needed clothing that could adapt to a wide range of professional settings. Her weeks vary significantly, from business-casual office days and “jean Fridays” to board meetings and customer dinners.

Together, we focused on building a versatile wardrobe that could move seamlessly across these environments. We selected polished pieces that worked for board meetings but could also be worn in the office, elevated dark denim for casual Fridays, and outfits that transitioned effortlessly into evening customer dinners.

A few weeks after our session, she sent me a note that perfectly captured the impact of our work. She was attending a board meeting in New York City. On the first day, she wore an outfit from before we worked together and noticed she didn’t feel as confident. The following day, she wore one of the outfits we had styled together—and the difference was immediate.

She told me she felt like she “owned the room.”

That is the power of dressing with intention. When your wardrobe aligns with your role, your environment, and your personal style, it doesn’t just change how others see you—it changes how you show up.