The casual leader: How to dress for casual Fridays

Ideally, we want to dress in a way that is an authentic reflection of who we are and what we do, while aligning with our personal values, vision, and goals, regardless of whether we are at work or off duty.

Often I get asked why it is that it’s easy to dress for work, yet outside of the work environment clothes are suddenly challenging and difficult to manage. How is it possible to have clarity around what to wear to the office, yet little or no idea when it comes to off-duty time?

A significant part of life is dedicated to work, and getting dressed each day in a similar outfit often takes away any indecision about what to wear. Organisational dress codes tend to remove any anomalies, and the working wardrobe can take on a sense of uniformity.

What this all means is that when dressing is influenced by company culture with little or no flexibility to embrace self-expression, it can be difficult to adjust to the fluidity of a casual wardrobe.

When dressing is influenced by company culture with little or no flexibility to embrace self-expression, it can be difficult to adjust to the fluidity of a casual wardrobe.

In my experience, organisational leaders who don’t have a clearly defined signature look or personal brand can feel tortured about showing up in casual attire. Imagine the reaction to a structured, suit-wearing CEO who rocks up for casual Friday or an off-site team meeting in a mini skirt and crop top. Although this is an extreme example, it’s fairly obvious that your credibility, not to mention your ability to lead a team, may be in question. Perhaps a better option would be jeans, a button-up shirt, and blazer—two parts business and one part casual.

I am not an advocate of conformity, and I love people to honour their uniqueness and individuality; but it’s worthwhile taking a moment to think about your personality, your values, vision, and goals and check in to see if they align with your signature look and brand. While you’re at it, take into consideration your company vision and values. You might be surprised by what you discover.