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Five Brilliant Tips To Dressing Like A Boss

The summer after my freshmen year of college I landed an internship at a global investment bank in Chicago. I had worked all through high school, but this was my first gig in Corporate America. My assignment was in the clearing department of the securities trading part of the business. This was a Swiss company with trading capabilities on every major exchange around the world. I was going to have direct contact with traders, brokers, etc. Clearing is a back-office function of processing the day’s trades. Because a family friend and my father had worked out this situation, my interview was very cursory and I didn’t really ask too many questions. The HR person said something about working on a line. My experience with working on a line was associated with physical labor. So on my first day at this prestigious global Swiss bank in the Chicago Board of Trade I wore jeans, a denim shirt, and gym shoes. And everyone else was in business attire. #epicfail

With my lesson learned, I showed up the next day dressed appropriately. The line the HR person referred to was an electronic line. Trades were processed by computers, not by hand. Fast forward to my third summer at the bank. There was a black woman who worked as a trade floor runner. She would come up to our floor at the end of the day to process tickets. Her outfits were very revealing, tight and/or short. She had been talked to about it several times. One of the white male managers asked me to speak to her. The assumption being I could relate to her better because we were both black. Being naive, I spoke to her. It didn’t go well.

One of my biggest takeaways from this experience was we should dress for the position we want, not the position we have. After graduating from college I took great care with my appearance. I looked to see what women two levels above me were wearing. The problem with that strategy was that there weren’t very many women two or even one level above me. All were white. And all dressed as if they were men. It was an endless parade of shapeless, colorless and sexless attire. I also saw black women constantly harangued for their outfits and hair in a way white women weren’t. It didn’t matter how professional the dress or how beautifully coiffed the hair. They wanted black women in the shapeless, colorless and sexless garb.

My college experience has come full circle. Now, as a leader in my organization, I’m seeing young women of all races coming to work in outfits that are great for the club, dates, or Sunday brunch, but not for work. I’m seeing male managers afraid to have courageous conversations about what is and isn’t appropriate. Black women can dress professionally, fashionably, and fabulously. The goal is to keep your clothing from distracting from your contributions. Follow these five simple rules for slaying in the workplace.

1. Observe the Culture and Environment

Not sure what to wear or if your personal style will fit in? Wear something neutral to work for the first week and observe the culture. How you would dress at a fashion magazine is very different from how you would dress at a bank. If it’s a dress down culture but you like to dress up, no problem. Make the appropriate adjustments. For example, if you wear a very nice suit complement it with understated jewelry and accessories. Also, find out if there’s a dress code. Some policies can be restrictive on types of shirts, shoes and what constitutes professional dress.

2. Complement Your Figure

Where some outfits go wrong is that they are ill-fitting for the body type. Black women tend to be on the curvier side, while clothes are largely made to fit white women. This makes it difficult to find the right fit, especially if you’re on a budget. The best tip is to find the size that fits the biggest part of your body then have it tailored. Let’s just put it out there. Society is uncomfortable with large breasts in professional settings. And when you have large breasts and a flat stomach or a smaller waist, they tend to stand out even more. Don’t cover them up to pretend you don’t have any, but don’t come in with a plunging neckline either. Unless, of course, you work in an environment where that’s appropriate.

3. Dress Like A Man Because You Want To

Love to wear high heels? Go for it, provided you don’t work someplace where that wouldn’t be safe. Yes, show off your legs. Wear some color. Ditch shoulder pads. In other words, it’s okay to look feminine. A good rule of thumb for dresses and skirts is they should hit you just above the knee. And, when you’re sitting your hem should not disappear revealing most of your thighs. The hem should rise about three inches or less. The tighter the fit, the higher the hem will rise. Keep your legs together and cross at the ankles to prevent showing your government business.

4. Your Style Should Enhance Your Brand

Let your style shine through. After you’ve taken the time to observe the environment, you’re ready to put your spin on it. Always be true to yourself and don’t feel the need to conform too much. If those you work with are more focused on your attire than your work product, it may be time to re-evaluate working there. The way we dress is a manner of self-expression. And while we may not get to dress 100% to our desires, we do have some wiggle room. Make sure your personal style doesn’t take attention away from your good work, but instead enhances your overall brand. After I finished business school I didn’t have a too much money to spend on clothes. But as my income increased, I focused on creating my signature style. I landed on shoes. I took great effort to find unusual and stylish shoes that were within policy. I started wearing four-inch heels because most of the men I worked with were so tall. Then, after a while, people always took note of my shoes, in addition to my work. Shoes were an easy way to dress up my more neutral outfits and suits. My shoes became part of my brand. When I walked into the room people were prepared for a great meeting, meaningful work, and stylish shoes. They also made me feel feminine.

Dress shabbily and they remember the dress; dress impeccably and they remember the woman. -Coco Chanel

5. Dress For The Career You Want, Not The Job You Have

Again, the best advice I ever received on workplace attire was to dress two, even three levels above me. The first person to tell me this was a white male. He pulled me to the side one day to show off his cufflinks, they were part of his signature style. When he was young, he saw all the managers wearing them. So he wore them too. Look up in the organization to the role you ultimately want, take note of what they’re wearing. I never worried much about out-dressing my peers. That rarely happened because they too received the same advice. One of my favorite quotes is from Coco Channel, “dress shabbily and they remember the dress; dress impeccably and they remember the woman”. In other words, never let your appearance be part of the conversation around your performance.

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Nile Harris
Nile Harris, the Chief Chick, is a word weaver and dream believer with 2o years of experience in healthcare and finance. This aspiring motivational speaker, TED presenter and LinkedIn Influencer is committed to valuing people, driving healthcare access and innovation, and weaving words that move people to action. Her views are her own.
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