Dressing For Work:  Part One of a Five-Part Series – Pink Ruffles at Work?

Now I’ve never been a slob, and always try to dress appropriately, but I’ve learned a few specific tricks over the years to help my appearance better “match” my authority and positioning as a leader…and sometimes even offset my rather carefree personality and soft voice, which can sometimes seem like a contradiction to my explicitly clear and direct communications style. And even though it may not be intentional, and no one should really give two licks about what you’re wearing, the fact is when your words don’t match what people see in front of them, your words lose a sh*t ton of power and effectiveness.

I’d like to share five specific questions I ask myself every time I get dressed for work. These questions help me to make better clothing choices that more closely match my intended communication goals.

#1. What percentage of my outfit is girlie?

Am I wearing something with pink ruffles? What about the shade of pink, is it a soft, pastel pink or a strong, bold pink? Does the pink ruffle account for 5-10% of my overall look or is it the main attraction? What about the other elements of my outfit? Have I paired it with strong or heavy textures like leather or soft unstructured or flowy materials? Is there a bow or any other traditionally “girlie” elements anywhere else on my body? Or does it stand alone, well-placed amidst other more tailored or “stronger” outfit elements?

When I get dressed, I have to think about “strength.” Does my outfit feel strong in some way? What does strength look and/or feel like to you? For me, strength feels like tailored, well-fitting and crisp clothing options. I realize strength may look and feel completely different for you. But for me, I prefer to stay away from the flowy, soft and light design elements, the ultra-feminine bows and ruffles and the super-popular-right-now boho looks for work. That doesn’t mean I won’t sport a pink ribbon or a little fringe here and there! It just means, when I wear that pink ribbon (and tie it into a bow no less), I’m also wearing a high-waisted heavily-structured grey pencil skirt, crispy tailored button down and serious-looking red power pumps. I feel best about my work attire when less than 15% could be considered “girlie” looking.

Of course, this may not apply to you at all. We all have a personal “vibe” we naturally give off. I’ve always felt mine was a bit too soft, sexy and/or feminine compared to the typical caricature of a made-for-television CEO type.

The good news is things are changing, women who rule the world are commonplace today. Well, in my utopia they are! Realistically, women only account for 4% of F500 senior executive roles, but they account for 39% of other management positions. And the perceptions of women leaders are evolving. The sheer variety of personality and style is making its way into the real world, where we no longer rely on some outdated stereotype of what a boss looks like. And people are getting used to (and prefer) leadership with authenticity, where the boss is expected to be a true representation of her own personality and unique qualities…all the way down to the attire she chooses.

It’s 100% okay and appropriate to be an ultra-feminine (both in dress and demeanor) person who also happens to be a badass executive leader, no-nonsense straight-shooter and authority figure with immense responsibility. Please know, these things are absolutely NOT mutually exclusive! I feel that I am able to be both feminine and a strong leader – at the same time. It’s just for me personally, I’ve found that I get a more desirable response to my directives and communications when I combine them with a stronger, less-girl-more-woman, overall look. I use strategic clothing choices to “make up for” what I perceive to be a potential weakness or shortcoming from my own “vibe” not really matching my words and therefore not providing me with the desired outcome from my audience.

What do you think? What kind of outfit makes you feel like the strong and smart leader you are today – or the one you want to be? Please share your favorite boss outfit in the comments – I would love to see pictures if you have them! Here are a couple of my favorite girly outfits…

dressing for work - pink ruffles

A cool pencil skirt outfit with a girly pink bell-sleeve top. The tennis shoes help provide a little tomboy.


dressing in pink ribbons for work

Another girly outfit with no less than a pink ribbon! I’ve been wearing this one for 10+ years. I referenced this outfit earlier.


dressing for work options

And here’s a clearer picture of my work bag from the first outfit…plus my cat Vegas.

Also, stay tuned for the next article in this Dressing for Work: Dress Like a Boss series. Learn the second question I ask myself each day I get dressed for work and how it helps me to be a better communicator.

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