Successful Women Share Their Personal Style

Clothes do not make the woman. But they can make her even better.

The daily grind of dressing and grooming rituals never ends, nor do the visual, sizing-you-up encounters with clients and coworkers. We all inevitably make our share of fashion faux pas as we refine our image. And while personal preferences and contexts vary, some aesthetic wisdom has universal truth.

I talked to five successful women with different styles and career trajectories about how they use their image to boost their success. Here’s what they shared.

The Look of Success

The Look of Success

Clothes do not make the woman. But they can make her even better.

The daily grind of dressing and grooming rituals never ends, nor do the visual, sizing-you-up encounters with clients and coworkers. We all inevitably make our share of fashion faux pas as we refine our image. And while personal preferences and contexts vary, some aesthetic wisdom has universal truth.

I talked to five successful women with different styles and career trajectories about how they use their image to boost their success. Here’s what they shared.

Nima Katz, fashion attorney at Nima Katz Law and co-founder of the Fashion Law Studio

Nima Katz, fashion attorney at Nima Katz Law and co-founder of the Fashion Law Studio

First, tell us about your workwear style.
First impressions are everything and the way you dress is your visual resume. When potential clients see me, I want them to know I am creative, relatable, and approachable. I’ve found that my clients are most comfortable when I’m not dressed in traditionally “lawyerly” clothing. For example, I’ll opt to wear a vintage Oscar de la Renta sequined blazer and high-waisted stone-washed jeans to a presentation, rather than a traditional navy skirt suit.

Why is image such an important part of your professional identity?
As a fashion attorney, it’s important for me to look the part! Moreover, communication is a major facet of my job. And my image affects that. How I present myself to clients determines whether they will hire me and trust my advice, and I also become a reflection of my clients to third parties. The image I try to convey is that I am part of the industry, like them, but am also a responsible and competent attorney who can handle serious legal issues.

What’s been the biggest challenge with your professional image?
I’ve always enjoyed pushing boundaries with my fashion choices, but sometimes it’s difficult to wear what you want and send the right message to your target audience. At big New York law firms, I found it challenging to incorporate my out-of-the-box taste into my conservative work wardrobe. Now, as a fashion attorney with my own practice, I face the opposite challenge — conveying a professional and serious image while choosing less-traditional options such as bold jewelry and statement pieces.

Tell us about a fashion faux pas you made and what you learned.
I got dressed for a work-related holiday party — in California — in a vintage black Yves Saint Laurent dress, with black tights, a wool Irish shawl, and my hair in a tight bun. When I arrived everyone was dressed in colorful, more weather-appropriate clothing.

I snuck into the bathroom, took off my tights, rolled up the sleeves of my dress, put on red lipstick, took my hair down, threw on a chunky vintage gold necklace I had in my purse, and stashed my shawl at coat check. Voila! I was California holiday-party chic. It was a good lesson in thinking on your feet and always having a plan B.

Have you ever had an aha moment about your style?
Growing up I was often told, “Only you could get away with wearing that.” But anyone can get away with wearing anything, so long as they wear it with confidence.

Can you give us one piece of advice on dressing professionally?
Authenticity is key. So when figuring out your professional style, give equal weight to the traditions of your profession, the audience you primarily interact with, and your personal taste.

Catherine Pickavet, copy editor at TechCrunch

Catherine Pickavet, copy editor at TechCrunch

First, tell us about your workwear style.
I work in San Francisco in the tech community, where the dress code is casual. So when I work from the office, I wear jeans, a T-shirt or a button-up, boots, and a hat. I am a masculine-of-center queer woman of color, and people often assume I’m male. My ambiguous identities determine how I navigate through the world and how I am perceived.

I’m 41 and no longer care what people think. “Hey sir, you’re in the wrong bathroom.” Whatever. I have a confidence now that I have had to fight to convey. And the clothing I have given myself permission to wear plays a big role in the confidence that I wish I’d had when I was growing up.

Why is image such an important part of your professional identity?
Though I may not like it, I understand that image is a part of professional identity — especially for women, who are sadly judged more based on their image. Because of the male privilege I have as a result of being masculine of center, it’s one I experience differently from many women.

Of course I don’t rock up to the office in baggy shorts and a pair of Lugz boots. But because of the struggles I’ve had from an identity standpoint, it’s important that I own what I’m putting out there.

What’s been the biggest challenge with your professional image?
When I was just starting out in my career as an editor almost 20 years ago, I had all of these preconceived notions of how a woman in the world was supposed to present herself. I grew out my hair in college because I didn’t want to be called “sir.” I used eyeliner (which makes me cringe now). I put on a show in order to give society what I thought it wanted: femininity. I took up the challenge of presenting a false version of myself, so as not to stand out as the “other” that I was.

Have you ever had an aha moment about your style?
My hair. First I grew it out and shaved it underneath — which was not a good look. Then I cut it short, until I unsuccessfully tried to grow locs. This is a much larger story, but I was in my mid-twenties, desperately in search of a racial and gender identity. I learned that my sense of self was going to come from within. That began my quest to find the person I was on the inside and match that with what I presented on the outside. I’m still on that quest.

Can you give us one piece of advice on dressing professionally?
It’s easy to say “be yourself,” isn’t it? That would require professional women to stop reading beauty and advice blogs and just go out into the world wearing what they want, presenting themselves in the most comfortable way. But that’s not how the world works. So be in the moment, own your look, and if you want to wear the latest pair of heels with a red sole, then do it because you don’t give a f—, not because you think you’re supposed to.

Fran Hauser, partner at Rothenberg Ventures and former president of digital at Time, Inc.

Fran Hauser, partner at Rothenberg Ventures and former president of digital at Time, Inc.

First, tell us about your workwear style.
Your visual identity is an extension of your brand, so I’m mindful of how I present myself. I try to communicate that I have a keen eye for innovation, a quiet confidence, the ability to lead, and an understanding of what appeals to modern women. I do this through classic, tailored pieces that also have a bit of an edge, like a black cardigan with a faux fur collar or skinny pants with small studs down the sides.

I also have a few go-to looks that feel authentic but allow me to dress quickly in the morning: skinny jeans with a great top, a chic day-to-night dress, and black leather leggings with dressy boots.

Why is image such an important part of your professional identity?
Venture capitalism is all about connections. Each week I have anywhere between 15 and 25 in-person meetings, many of which are first meetings, and generally attend one or two events. That adds up to 50 to 100 first impressions every week. Your visual identity is the first thing people see, so it’s a big part of the initial impression that you make.

What’s been the biggest challenge with your professional image?
In the startup world, many of the people I meet with are 15 years younger than me and tend to have a more casual, breezy style — so the outfits I wore as a corporate media executive simply don’t translate. The biggest challenge has been adapting to the casual tech style while remaining true to my personal style. It’s a work in progress, but I’m getting there!

Tell us about a fashion faux pas you made and what you learned.
That would be the first (and last!) time I wore a maxidress. It looked completely ridiculous given my petite size. The lesson? Just because something is on trend does not mean it will look good on you.

Have you ever had an aha moment about your style?
When I met Paula Thomas, the creative director and founder of Thomas Wylde, I fell in love with her line, which is full of statement pieces. I realized you can wear a super simple foundation, all black or a turtleneck and jeans, and then layer a statement vest, cape, or shawl over it for a showstopping but not over-the-top look. This also makes getting dressed very easy.

Can you give us one piece of advice on dressing professionally?
Be true to who you are. Focus on what makes you feel comfortable and what feels authentic to your personality rather than what’s on trend. Confidence goes a long way in self-presentation, which is why it’s so important to wear what makes you look and feel your best.

 

Jennifer Deare, president and founder of Deare2, a marketing agency

Jennifer Deare, president and founder of Deare2, a marketing agency

First, tell us about your workwear style.
I try to communicate that I’m intelligent, creative, and a pro, while still coming across as approachable and attractive. I operate in a highly competitive marketplace where people’s impression of you tends to stick. There are some standard agency looks, but I want to communicate that “I’m successful and to be taken seriously — but I have flair.”

Why is image such an important part of your professional identity?
Advertising and marketing are image-based businesses — the thought process is that if you’re creative and with the times, you’re connected to what’s going on. Showing I’m “with it” sends the message that my clients will be successful if they do business with me.

What’s been the biggest challenge with your professional image?
Staying in style, but still looking professional. I don’t want to wear the latest fashion if it is going to give people the impression that I am a middle-aged woman trying to dress up like a 25-year-old.

Tell us about a fashion faux pas you made and what you learned.
It involved someone I interviewed: A beautiful girl walked in wearing an expensive fur coat, Louboutin shoes, and an Hermès Kelly bag. I thought, I would never hire you. I can’t imagine how uncomfortable my clients would be. It’s one thing to say “successful.” It’s another to say, “I don’t need to work.”

Have you ever had an aha moment about your style?
My aha moment came when I hired a stylist to help me understand what looks good on me and what image I was projecting. Previously, I always dressed in what I liked on other people — but those clothes were overwhelming to my small frame. What I was buying didn’t fit who I was.

Can you give us one piece of advice on dressing professionally?
Get a professional opinion. It is very hard to see ourselves the way the world sees us. I was always lucky to be small enough to fit into the latest fashions, but I was something of a fashion victim, looking to fashion magazines to know what to wear.  Also, my wardrobe was unwieldy and it was hard to put outfits together.

I spent a tremendous amount of money on expensive clothes to get a professional look when I could’ve mixed a few good pieces with some less-expensive pieces or accessories to finish the look. And packing was a nightmare. Now I pack a few pieces that all go together and re-wear things without anyone realizing it.

Cheryl Yeoh, CEO of Malaysia Global Innovation & Creativity Center and serial entrepreneur

Cheryl Yeoh, CEO of Malaysia Global Innovation & Creativity Center and serial entrepreneur

First, tell us about your workwear style.
I try to visually communicate that I’m a strong, contemporary professional, but not too corporate. Since I’m heading up a big government agency at a relatively young age, I have to dress to convey that I’m in a position of respect and power, but also keep a down-to-earth and friendly tone.

I like styles that are classic but youthful, with a hint of startup identity. I tend to wear a lot of dresses or skirts that have solid colors and clean cuts, and I like to pair them with bold accessories. When I wear jeans, I pair them with a silk blouse to balance out the casual denim.

Why is image such an important part of your professional identity?
It conveys that I take my profession and the people I work with seriously. In today’s diverse workplace, people tend to judge you at face value, so I would rather not be mistaken at first impression. I want to visually project my personality, competence, and commitment, because that establishes trust quicker. If I don’t manage my image myself, others will.

What’s been the biggest challenge with your professional image?
I tend to look younger than I actually am, and sometimes people don’t believe I’m the CEO. Hence, my biggest challenge is to look my age and appear to be someone in power. But I don’t like wearing suits and jackets because it feels too stuffy for me. I also don’t carry designer bags or wear designer shoes or watches, even though I can afford it.

I want to stay true to my personality and character. Unfortunately, sometimes people judge me for that, especially in Asia. But it’s something I’m willing to compromise because I want my image to convey my values.

Tell us about a fashion faux pas you made and what you learned.
I once wore suit shorts to speak on a panel, and I would never do that again. Always wear long pants or a knee-length dress and closed toe shoes when speaking on stage. I’ve also started investing in a professional blowout whenever I speak at an event or attend an interview with photographers or reporters. I used to do it myself, but you’ll never look as professional, and yes it does make a difference when the photos come out.

Have you ever had an aha moment about your style?
When I discovered the casual wool-flannel blazer at Uniqlo that’s really comfortable but looks professional. I can wear it on top of most outfits and it instantly makes me office-ready, but isn’t stiff like a suit jacket. Adding a scarf to an outfit also gives it an elegant boost.

Can you give us one piece of advice on dressing professionally?
Dare to be yourself first, and then figure out how to tweak it and present yourself to best suit your environment. You’ll perform best when you feel comfortable in your own skin, but you’ll perform even better when you supplement that with being dressed in a way that demands respect.

Anna Akbari, Ph.D. is a sociologist, entrepreneur, and the “thinking person’s stylist.” She is the founder of Sociology of Style, which takes an intelligent look at image and culture-related issues and offers holistic image consulting and life coaching services. Find out more and follow her on Twitter.

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