Rethinking Business Casual: From Confusion to Strategy

What does “business casual” even mean anymore? Let’s unpack it. Where it started, how it’s evolved, and most importantly, where we go from here.

While speaking at a recent Women’s Conference, a VP from DirecTV pulled me aside and said:

“Susana, I find ‘business casual’ really confusing. I’m never quite sure what’s appropriate. And to make it harder, some of my younger team members don’t seem sure either. One shows up in a hoodie, another looks like she’s headed out for the night. I’m stuck in the middle, wondering what to say or how to set the tone. Can you help me make sense of it? For myself and my team?”

That moment stayed with me because I hear versions of this conversation all the time. From women navigating leadership, culture, and visibility.

Let’s take a quick walk through history to explain how we arrived at this vague and often frustrating concept. And how we can move forward with clarity and intention.

A Brief History of Office Dress Codes

In the 1950s, officewear for women was strictly formal: stiletto heels, stockings, neatly tailored dresses. Every single day. Style was sharp, but rigid.