The Hidden Struggles of leadership as a female

A deep dive into style and the impact it has on our ability to lead.

Learning to embrace my body and understand who I am after becoming a solo parent was tougher than I can explain really…but I will try. 

My career was everything to me, I was a successful teacher and my leadership skills were praised by others - it would be true to say that at work I was at my very best. The success felt natural and really provided my life with its value I suppose as I gave most of my energy to it and thrived in the high pressure environment.

But 5 months after birth I was seriously struggling to maintain my professional status whilst parenting an infant and trying to balance the books.  The harder I worked, the less I prioritised myself and the more I became riddled with anxiety about my figure. This feeling wasn’t new, during my teenage years I suffered with insecurity about my weight which came flooding back due to the toxicity I faced in my household.This was made so much harder because I just could not find anything to wear.

Classic work wardrobe - the go to look.

I learnt very quickly the power of a great outfit. 

Like many women I speak to, I became acutely aware as an adult of how I truly felt about myself and was even more determined not to pass those insecurities on to my children. So, during my own journey of recovery and stability after childbirth, a breakup and a bumpy return to leadership, I made a conscious decision to do the work on myself and create a more positive environment at home. What I did not expect was that this process would eventually lead me to establish Jessica Steward Styling, a personal styling brand with a mission to help bright, articulate women overcome their struggles with inner confidence through An Education in Style.

For me, personal styling is about far more than just a wardrobe full of new clothes. It is an opportunity for career driven women to feel empowered, confident and stylish, giving them the tools to show up in the world as the best version of themselves.

So far, I’ve found that supporting professional women in overcoming their insecurities is what feeds my soul. Styling isn’t just about clothes, it’s about self-expression, empowerment, and feeling like yourself again. My signature styling service, An Education in Style, is designed to help women challenge harmful societal standards around thinness and youth while curating a wardrobe that makes them feel stylish, comfortable, and confident in their own skin. Because true style isn’t about fitting in, it’s about showing up as your best, most unapologetic self.

My experience styling women in leadership roles often revolves around a common insecurity: they struggle to believe that, despite leading massive teams, making high-stakes decisions, and navigating complex challenges, they still feel lost when it comes to choosing what to wear. I believe this struggle for mid-life professional women is rooted in a psychological dysfunction caused by being raised by women trapped by the patriarchal norms that society pumped out. We are socialised, even nurtured, to feel inadequate about our appearance so that men, via capitalism, can profit from our insecurities.

I can only claim the status of an armchair psychologist, though I am an avid reader when it comes to mindset and body image. I am, however, a qualified sociologist, and my studies have always revolved around the idea that there is a clear relationship between the norms we learn during primary socialisation and our behaviour as adults. If childhood taught you that you were ugly, fat, stupid or any number of other hideous labels, then adulthood is often laden with those deep rooted fears.

These days I consider myself more of an observer, and I have become fascinated by how people interact and the sheer number of snap judgments we make. It is remarkable how final these judgments can feel. Our brains rely almost entirely on what we see before us, and that initial impression can shape so much of what follows.

Unsurprisingly, then, we yearn to see something pleasing when we look at ourselves and others and certainly not something that triggers a negative response. In fact, a negative reaction to our own reflection can be so visceral that it makes us feel physically unwell. Since we can’t control this instinct, the only way to ensure we like what we see is to be intentional about how we present ourselves.

This is why women carry emotional baggage around clothing that goes far beyond simply wanting to look “good.” We are biologically conditioned to seek approval from an observer, to positively stimulate their visual perception. For women, this expectation is heightened, and for those in leadership, it becomes even more critical. While the standards of who we need to please may shift depending on the context, one thing remains constant: we will always be wearing an outfit.

I see this time and again with accomplished professionals who exude confidence in their expertise yet feel completely adrift when it comes to their personal style. It is never just about the clothes. It is about the energy behind the outfits they choose to wear. I urge women in leadership, whose time and mental space are precious, to stop the cycle of decision fatigue that leads to grabbing a “throw-on” outfit and to consider how much they truly value themselves with that mindset.

Every single client I have worked with has shared that the impact of getting their style right went far beyond simply looking good. From promotions to career changes, new relationships to embracing new lifestyles, each and every one of them has discovered a sense of personal growth after investing in their personal style.

I may just be providing the secret weapon you need to glow up for real.

Thanks for reading,

Love Jess

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