What My Daughter’s Mini Mouse Dress Taught Me About “Dressing for Success”

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What you wear affects how you think, how you feel and even how you work, so approach your style like you approach your startup: Make it your own.

By Maya Kramer (Co-Founder & Chief Styling Officer, Stylit)

I took my daughter out to celebrate the start of her summer vacation with breakfast at a local café. On the way home we ran into a friend of mine who noted my daughter’s outfit:

“Oh... you usually dress her in such chic outfits.”

To be fair, my daughter was wearing a slightly oversized Minnie Mouse dress complete with frilly shoulders, a bright red polka dot skirt and a mouse-ear headband. But her outfit elicited exactly that kind of backhanded compliment because of the misplaced expectation that, since I work in the fashion industry, I should be following every latest trend. Not only that, but I ought to be forcing these looks on my daughter, making sure she wears something that conforms to them every day.

What this woman had completely failed to understand was the crucial difference between what fashion and style were meant to be, and how they’re perceived today.

Style Does Not Mean ‘Fashion’

While not necessarily a perfect example of a currently “trending style,” my daughter’s choice in clothes was in fact the perfect example of what style is supposed to be – a form of pure self-expression.

That morning when she opened her closet, my daughter decided that the best way to express her excitement at our coming breakfast date was to flaunt a dress that would have made Walt Disney proud.

For her, the Minnie Mouse dress told the world that she was feeling amazing and that it was going to be a great day. “Chic’ wasn’t a consideration; the outfit she chose was meant to make her feel good – it wasn't about keeping up with the latest fashion or pleasing anyone else.

Express Yourself

Style is an often underrated tool for self-empowerment and, even more importantly in a business context, it can help drive creativity and initiative. Developing an awareness of the power of style can also be something that informs the business strategy of any company.

Style isn’t about this or that runway look: It’s about using fashion or clothing and accessories to say something about ourselves that matches who we think we are or want to be.

When we choose our outfit each morning, we are taking a step in defining what that day is going to be like for us. What impression are we seeking to give off? What mentality do we want to put ourselves in?

To those who would minimize this approach by connecting it with a materialistic perspective, think about the professional athlete in soccer, basketball or football. The process of putting on a uniform is a physical manifestation that game time is approaching – it's only clothing, but for many athletes it helps them turn a mental switch.

Stylish Technology

In 2012, I was approached by a technology entrepreneur who wanted to discuss an idea he had to marry technology and fashion into a new startup. We met shortly after and came up with the concept that served as the foundation for Stylit, a technology that combined professional stylists with algorithmic training technologies, to create a personalized styling platform that would allow any woman to more easily use style to express herself.

But the secret sauce – the one that took us from 1,000 to 100,000 users – was that we didn’t set out to simply merge fashion and technology. Instead we tried to create an environment where two worlds that were normally considered separate and incompatible were allowed to interact closely, and let experiences and concepts from both drive innovation in the other.

Importantly, the influence of this ideology wasn't limited to our product and, while style hasn’t been validated as an expertise worth having (especially not in the tech world), it can be a powerful tool that actually impacts everything from productivity to creativity.

Appearance on the Outside, Mindset on the Inside

The startup world is filled with many creative people but, by and large, it has a pretty default dress code. Entrepreneurs wear t-shirts – ideally with their startup logo across the chest – shorts and flip flops.

While there’s certainly nothing wrong with this uniform, it doesn’t necessarily reflect the wide variety of startups and startup employee personalities out there.

Walk into an office of t-shirt wearing colleagues in a suit, and you’ll likely going receive a myriad of comments on your choice of dress. Some people work better in more casual attire, others will need something more corporate to influence their mentality at work and still others succeed with some combination of the two.

Though it's easy to say that this is a minor issue compared with the other fundamentals of running a business, the truth is that when self-expression is muted in one form, it can lead to decreased expression in other areas as well.

Cultivating Creativity

Creativity is about tapping into the unique perspective that we bring to the table. The more actions we take that reinforce our confidence in our own creativity and viewpoint, the more likely we will be to let these facets shine through in all our endeavors.

For many, the clothes we wear are the first chance at expression we get during the day. By embracing this, we channel the approach to the rest of our actions, not to mention the benefits we get from the confidence in looking our best.

When developing a company culture, we all aim for inclusivity. But sometimes in the pursuit of being laid back, we foster an environment with a different kind of conformity. Actively encourage different personalities and forms of expression in your office and watch the benefits of bringing different approaches and perspectives together.

Fostering creativity certainly isn't limited to having a wide array of outfits in your office, but as our first form of self-expression each morning, it certainly doesn’t hurt.

What do you do to boost your self-confidence?


About the guest blogger: Maya Kramer has over a decade of experience in the fashion industry. She started as model booker, and then became a fashion producer for world class brands and magazines including Saks Fifth Avenue, Condé Nast, Net a Porter, Victoria’s Secret and Esprit. Along with teaching yoga and spending time with her daughter Hila, Maya enjoys fulfilling her ambition to make styling accessible to every woman in this world.