When I sat down with Jenny Eversole, co-founder and CEO of StyleSpace, one thing became clear right away: style is about much more than what we wear. It’s about confidence, personal branding, and the way we show up for ourselves, our teams, and our organizations.
Jenny has built her career around this idea. As a former couture fashion designer, she saw firsthand how style could transform her clients’ confidence and opportunities. “It changed the places they went, the conversations they had, how they felt about themselves,” she told me. That realization inspired her to launch StyleSpace, a platform that helps individuals and teams “look, feel, and present the most confident, elevated version of themselves that ultimately represents their leadership potential.”
Our conversation centered on the way style influences culture, engagement, and leadership in a modern workplace where the rules are less defined than ever.
The Evolution of Workplace Style
In the last five years, workplace attire has changed more than it had in the last hundred. With the shift to remote and hybrid work, dress codes have loosened, and in many organizations, they’ve disappeared entirely.
“When we start to work with teams, I’ll ask for their updated dress code,” Jenny said. “And I’m shocked at how many Fortune 500 companies don’t even have one.”
That lack of clarity leaves employees guessing, creating anxiety and inconsistency. For new hires, the challenge is even greater. “Imagine being an intern walking into your first day of work and not knowing what’s appropriate,” Jenny explained. “You want to make a good impression, but you don’t have any guideposts.”
Style as a Strategic Advantage
Jenny and her team focus on helping individuals and organizations align their outward appearance with their inner intentions, rather than simply chasing trends.
“Your visual presence — the energy and confidence you bring — that’s what sets you apart,” she explained. Whether you’re in the office or on Zoom, how you show up matters.
Jenny gave the example of a client in finance who wanted to stand out in a sea of black suits and white shirts. “He started wearing a sleek black sport coat with a black collared shirt. Simple, sharp, and memorable,” she said. “It elevated his look without making him feel overdressed or uncomfortable.”
True confidence comes from authenticity, not imitation. Jenny cautions against adopting someone else’s personal brand, like the iconic Steve Jobs black turtleneck. “People make the mistake of trying to adopt someone else’s brand,” she said. “We need to define our own.”
The Confidence Gap
One of the most striking statistics Jenny shared is that 96% of people believe their style impacts their leadership potential, but only 15% feel they’re dressing in a way that reflects that potential.
That gap has real consequences: missed promotions, lack of visibility, or simply feeling less confident in high-stakes settings. But transformation is possible. After completing StyleSpace training, 92% of participants report feeling more confident, professional, and engaged.
“It’s not about telling people what not to wear,” Jenny emphasized. “It’s about helping them feel comfortable in their own skin, and defining their style within the context of their workplace.”
Personal Branding Meets Organizational Identity
Organizations wrestle with balancing individuality and company culture. Many leaders want their people to express themselves, but they also need a unified, professional image for clients and stakeholders.
Jenny believes style is the bridge between the two. “It’s individuals who are building those trust relationships,” she said. “When you develop your personal brand identity in a way that reflects the organization’s values, everyone wins.”
Some companies are even putting resources behind this idea. Through StyleSpace, teams can schedule interactive workshops, and employees can opt into one-on-one styling sessions, often covered by professional development budgets or employee benefits.
Practical Advice for Individuals
Here’s Jenny’s advice for anyone looking to elevate their personal brand:
- Define your adjectives. Decide how you want to be perceived (trustworthy, innovative, or approachable) and let those traits guide your choices.
- Focus on versatility. For remote professionals, invest in pieces that elevate your “waist-up” presence for video calls. For in-person events, consider signature accessories or colors that make you memorable.
- Prioritize fit and confidence. “It’s not about the most expensive clothes,” Jenny said. “It’s about finding what feels right and represents you well.”
She also points out that small details make a big difference. For example, adding a sport coat to a T-shirt for a client Zoom call can signal that you take the interaction seriously without making you feel overdressed.
Style as Empowerment
At the heart of Jenny’s message is empowerment. Style gives you the confidence to step into spaces ready to lead, contribute, and connect. As Jenny explained, “Before you even introduce yourself, you’re telling people who you are and whether they can trust you. That can feel daunting, but the empowering part is that you’re in full control of that narrative.”
“It’s the most powerful nonverbal expression tool,” she explained. “Before you even introduce yourself, you’re telling people who you are and whether they can trust you. That can feel daunting, but the empowering part is that you’re in full control of that narrative.”
A Call to Leaders
For leaders, Jenny’s insights offer a challenge: rethink the way your organization approaches style. Not as a rigid dress code or a trend-chasing exercise, but as part of your culture, or a way to help people feel confident, connected, and clear about how they show up.
Confidence is contagious. And when individuals feel empowered to represent their best selves, teams and even entire organizations rise with them.
Brandon Laws is a workplace culture and leadership enthusiast, host of the Transform Your Workplace podcast, and VP of Marketing and Product at Xenium HR.