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The Fun of Getting Dressed

Updated: Apr 16

POV 8:00 p.m., the night before your first day at your new job:

You’re standing in your closet staring at the rack of clothes and wondering… what will you wear to work tomorrow? 

Sure, in the interview they said the office was business casual, but how casual IS the casual? And what do they actually mean by the business-y part of the  “business” dress code?

Also, what are you going to do with your _______fill in the blank (locs, braids, twists, naturally curly hair, long straight hair, etc.)  Is this a pull-it-up and pull-it-back ponytail situation? Or a flat iron/blowout, headband occasion?

And then you remember that “Bring your whole self to the workplace!” essay you read on Medium.


A woman posing

Can you really bring your whole self to work?

And, if you do, how will it impact the way that others see you? Treat you? Will you be awarded opportunities, or denied responsibilities based on the way that people perceive you solely by your personal appearance? Also, when did the simple task of getting dressed become a situation loaded with such potential significance? And WHO TOOK ALL THE FUN OUT OF GETTING DRESSED???!!! 

In the era of diversity, equity, inclusion, and belonging, how do you even show up without being exhausted by the gauntlet of semi-political choices you have to make before 7:30 a.m.?

2024 Truth: Being successful in a professional working environment requires that you recognize and acknowledge the tension that exists when you are creating an image that fits into your organization's culture, while still honoring who you are authentically. 

In her newest book, Executive Presence 2.0: Leadership in an Age of Inclusion, Sylvia Ann Hewlett builds on her groundbreaking work to research and define the traits of executive presence, that essential quality that all great leaders have that inspires us to follow them. Of all of the components of executive presence that Hewlett identified in 2012, then revisited with new research in 2022, the trait that was most changed in the decade was appearance

She notes that though appearance constitutes a mere 5% of the qualities considered essential for executive presence, it is often underestimated and misunderstood. “In reality, a person gets to make a first impression only once; if you blow it, you don’t get a second chance. …if your appearance telegraphs you’re clueless, no one bothers to examine the depth of your gravitas.”And most importantly? “Authenticity” is the 2nd most important appearance trait, behind “polish”, that is required for leadership success.

A woman posing wearing a yellow dress

Dressing with thoughtful authenticity to who you truly are can communicate your cultural awareness and your self-confidence. It allows you to connect with peers on something other than punch list items and gives other employees the space and permission to be vulnerable and true. It is a soft skill with a tremendous ripple effect. So what does your appearance or the way that you dress communicate about you? What are the risks of getting it wrong? 

Let’s think about “a finished look”, often referred to as  “polish”.   It’s one of those know-it-when-you-see-it things, that a person’s outfit feels cohesive, their accessories, shoes, and outerwear all create a look that is visually balanced and appropriate for the occasion.

A look like that doesn’t happen by chance. It requires awareness, planning, intentionality, and a thoughtfulness about details.

Awareness to understand the type of meeting or event that you will be attending and the people who will be there.

Planning to think through what you want people to feel about you. How do you want to be perceived? What do you want your clothes to communicate about you before you even begin to speak?

Intentionality to ensure that you have acquired all of the pieces that you need to create the outfit, including foundationwear and accessories, whether you purchased them new or thrifted them from your favorite secondhand market.

It all matters. How you show up will affect your career path, and ultimately your income. What happens if your look isn’t finished? Or if your look isn’t even really a look but instead just clothes that you threw on? Someone meeting you for the first time might think that you don’t have an eye for detail, that you don’t plan ahead or manage your schedule to provide enough time to ensure that your clothes are clean, pressed, fit well (regardless of size), and coordinate. Maybe they think that you don’t understand or care that others will judge you, which also might signal that you are unaware in social situations, something every smart employer understands is dangerous to client and co-worker relationships.

It’s a lot to process - and, in a perfect world, people wouldn’t make snap judgments based on appearance - but we must acknowledge that humans are visual and this is the world that we live in today. 

A woman outside carrying shopping bags

I’m not telling you to show up in a suit with a Brazilian blowout. I am telling you that it’s worth your time and energy to think deeply about the impact of your clothing and the attention that you give to your appearance. Step back for a minute and remember how you feel when you know you’ve nailed your look. You stand differently. Your shoulders are relaxed and you look people in the eye when you speak to them. Your emotional and intellectual energy can focus on the tasks at hand, and you aren’t distracted by the nagging worry that your shoes are too scuffed or your bra strap is showing.

When you show up feeling beautiful you are unstoppable.

In this post-Covid era, everyone is confused about what to wear to work, but investing the time and energy to determine what is appropriate for your workplace and still feels authentic to who you are is critical to your success.

So, Superstar, what are you going to wear to work tomorrow?


Photography courtesy of and written by Stephanie Grabow of SG Style Collective.

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