Being Stylish and Belonging in Tech: From Trying to Fit in To Expressing Yourself In a culture of Hoodies And Jeans

“What does a leader look like?”, is a question we come back to here often, and this time, we take it literally: I meet with five exceptional senior leaders to talk about what it’s like being interested in style and fashion in tech, of all places, where it’s long been seen as most fashionable not to care about these topics, where an implicit but strongly-enforced dress code of dark hoodies, t-shirts, and jeans reigned, and where the resulting “uniform” culture has been hard on everyone who doesn’t fit traditional ideas of what an engineer, a “technical person”, a “geek”, a leader looks like. So, how do you convey that you are all of those things, when you don’t look like the stereotype of someone who is? We talk about our journeys in attempts to fit in, exploring ways of expressing and being ourselves, and the stressful mental gymnastics involved in calculating how our appearance may support or undermine how we’re viewed and treated. We dive into being “firsts” in visible positions, and how we found style as a tool for empowerment, connection, and representation, and close with some favorite styles and recommendations to find your own. I loved having this conversation, and I hope you enjoy it too. “I think style and fashion is such an important part of self-actualization, and becoming that greater version of yourself, and it is a big part of how people perceive you, so it gives me great joy to feel self-actualised on a particular day and feel like I am representing the true version of myself.” — Christina This conversation was recorded in October 2024. Find the full episode transcript here.