Leadership, Fashion and the Future

The Tara Dress by Jennifer Hamilton for Prim & Wilde

The Tara Dress by Jennifer Hamilton for Prim & Wilde

I recently had the pleasure to be introduced to Leadership Training expert Jessica Osedach while we were both spending the weekend at an exquisitely renovated home in rural Vermont. Over fine wines and gourmet food, the dinner party conversation started with a lyrical debate about success and whether leaders are born or made, but was quickly corralled by Jessica's experienced point of view and captivated by her crisp insights and laser-sharp vision of leadership in a changing world.

Back in Manhattan, I immediately jumped on the opportunity to ask her to share some of her insights on women, leadership, success and of course...style, with me.

We met at a cosy coffee shop in the heart of the new financial district of Manhattan – midtown. I could spot Jessica from a distance, striding across the Rockefeller Plaza – an extraordinary blend of delicacy and strength, which she extends to her business wardrobe – she wore an elegant ivory shift top with a pair of tailored pants, topped with a magenta silk jacket.

PW: What does leadership look like?

“Leadership is conveying confidence, even in the face of not knowing, or in the face of challenging situations.  It looks polished, 'put together,' elegant as opposed to noisy.  It's like the eye of a hurricane - remaining calm and composed even when surrounded by chaos, change, swirling priorities.”

Jessica explained to me that seniority itself is actually an important part of leadership. Seniority is not just the time spent learning and growing, but the ability to share, coach, mentor that comes with experience. We are constantly growing and a leader knows that they can share their knowledge because they are still learning. But seniority does not only come after 20 years in a position, it is a constant that starts with each accomplishment. Transparency is key to leadership.

How do women feature in your program? 

“Women in executive level roles are still a minority in some functions but their numbers are growing.  In our program our women participants are equal to men in every sense of the word.”

How do women react to leadership?

“Every woman reacts differently - some may initially be anxious about being in charge, others act as though they were born to take that role.  I really think that we've arrived at a time where individual differences between women drive how they react to leadership, as opposed to their gender alone.  There are so many different kinds of women!”

How do women lead differently?

“I don't think that they do.  On the whole you have tough authoritative bosses, you have more collaborative bosses - I don't think that gender drives the majority of these differences anymore. It has to do with who these bosses are...their gender along with hundreds of other attributes. I will say that women may have a more complicated landscape to navigate. Appearance does matter more for women...tone might matter more. Think of Hillary Clinton. Is Bernie Sanders really that much more 'like-able' than her or is she being held to a different standard?”

Is it totally superficial to consider your appearance?

“Not at all.  It's critical. For better or for worse people start to form judgments about other people upon first sight.  In the workplace, how you choose to 'show up' – including what you decide to wear – is part of your professional image. It's better to be intentional about this than to ignore it.”

What could women do to make themselves better leaders?

Let me preface this by saying that I found this to be the most interesting part of our conversation. Jessica stunned me with the simplicity and vulnerability of her answer. She told me that emerging leaders “should be open to feedback and willing to change.  Remain flexible and adaptable.” Jessica recommended that everyone do some soul searching to make sure you know what you want in terms of career goals and that those goals will actually make you happy. Then go for it.

Thanks Jessica. I consider myself so fortunate to be able to meet and talk with women who can so brilliantly talk about their work and Jessica, like the leaders she works with, is truly transparent and willing to share her knowledge.


How to dress for an interview

Let's start with the premise that interviewing is fun. It really is – you are creating your best “you” and taking it to meet other people.

Have you ever packed for a solo trip to another city? You pack your favorite “you”, your ideal version of yourself (or even a fantasy self) – you browse through your favorite clothes, or shop for new, you choose ones that you know will look great on you. You are creating an image, you have no history and no future – all that exists is the “now”.

  "You are creating your best you"


Going to an interview is the same. You take your sharpest mind and your sleekest look and wrap them with the ribbon of self-confidence.


No matter what the position you are applying for, it's a no-brainer that you want to look professional, crisp and confident. Any other website is going to tell you how to don a dark suit and a white shirt. But more than that you want to look interesting. While you need to fit in, you really want to stand out as someone ready to attack any problem head-on – so you want to incorporate your own style into your interview outfit and show a little of your personality in your dress.

Know your body type and dress accordingly.

A sleek, well-fitting suit is a go-to solution, but maybe an office-chic dress with a coordinating jacket or a long-sleeved classic shirt with a well cut skirt. What looks best on you will be determined by your body type. We don't need to tell you that your shoulders should always be covered, you should not be showing cleavage or any thigh above the knee. Dignity is key, but the super-fun part is that you are going to enjoy dressing up.

Look like you

Dressing the part, is dressing as “you in the part”. Take time to savor the process of getting dressed in the morning, choose the right bag and shoes, the earring and necklace. What can you include that gives a hint of your unique style? You are not imitating someone else, you are bringing out the best “you” so don't hide beneath your interview costume.

The people who are sitting across the desk, throwing questions at you, are hoping that you will be the right person for the job. It's a game. A high stakes game, but undoubtedly one that you want to win.

Interviewing is the sales job of a lifetime.

Get dressed. Work Hard. Have fun.

Find us on facebook, twitter or instagram and tell us how you dressed for your best interview.

What To Wear To... A Pitch Meeting

As an entrepreneur you are, at some point, going to come face to face with an investor or a client, you are going to pitch your business and you need to be able to look professional, polished but modern and stylish – just like your business model – streamlined, modern and efficient.

Huge amounts of money can change hands and you need to look as if you are as professional and responsible as your awesome pitch presentation.

So what to wear?

We asked, Brigit, Kalena and Eleni and from PR agency Antenna (antennagroup.com) for some expert guidance on what to wear and when.

“As a PR company we are constantly pitching,” says Senior Account Executive Brigit, “we mainly represent tech, energy and life sciences companies, so we find ourselves in front of clients that range from very traditional to very relaxed. You need to do your research and find out who you are pitching to and how they dress. If we are meeting a client in the financial sector, we have to dress appropriately in a blazer, heels, skirt and very polished hair. But this can be a turn off in a different sector, for example if we are at a tech meeting then the look is going to be much more relaxed.”

“My go-to look is a pencil skirt and one statement piece that pops, but does not distract” adds Kalena Gravina, “with a well-fitting, chic pencil skirt you can fit into almost any meeting. You can dress it up or dress it down as the occasion demands and you will always look professional.”

“Read the situation,” says Eleni Polychroniadou.

If you are meeting at an investor's venture fund office with partners or to make a presentation, you will want to be dressed in a way that at least meets the dress code of their office. You want to look like a professional who will responsibly spend the millions that are on the table, and will be able to increase the investment in spades.

But if you are having a casual coffee around the corner then you can afford to be a little more relaxed, but still professional.

They all agree that you want to have a flexible wardrobe – a handful of key looks that you can make work for the clients that you are meeting. It makes a difference whether you wear a straight or a flowing skirt. A woman just has to be more conscious about how she looks, “I changed between events once,” says Brigit, “I realized I was the only woman and felt out of place in a skirt. My go-to tech pieces are chic skinny black jeans, a nice shirt and a pair of stylish flats.”

What is their best advice for a business woman pitching to clients or investors?

“Make sure if you are the youngest person in the room, you don't dress as if you are the youngest person in the room” says Kalena.

“And be certain that your words are the most important thing that people are going to remember.” adds Brigit. “Dress to show that you are a talented professional who has earned her position at the podium”

Thanks to Grind Spaces for their help, and for providing a great space for entrepreneurs to work in NYC!


We live in a brilliant era of entrepreneurial development, as an increasing number of women are breaking with convention, quitting the corporate world and driving change in the free market.

We work out of Grind Spaces in NYC's garment district and are honored to be surrounded by so many brilliant people who are building new companies that can and do change the world. And when we all work in our chic co-working office or on days when we work from home offices, gathered around our laptops on someone's living floor we can dress as we wish. The entrepreneurial world is famous for being low-key and casual, but the truth is, we all need to know how to step it up when necessary.