AnnaMarie Houlis
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Working professionals are told time and time again to dress for the job they want. So you might be wondering: how do you dress like a boss, if that's what you aspire to be?

How do women in leadership roles dress?

We asked women who've been promoted into leadership roles why and how they changed (or didn't change) their wardrobes as they advanced in their careers. In other words, what exactly should a manager wear, and what do powerhouse female CEOs wear?

Here's what they had to say.

1. Dressing like a boss means being comfortable and appropriate.

"I became Associate Director at OggaDoon this year at 28, and I knew immediately I didn’t want to change the way I dress; I’ve worked hard to get where I am, and it’s my skills and expertise that makes it possible for me to excel in my role," says Emily Perkins. "In our workplace, we encourage casual to smart casual depending on the day. The creative sector certainly has more flexibility than other industries, and I think ‘dress like a boss’ should be a balance of what makes you comfortable and what your industry expects of you."

2. Paying more attention is key.

"I earned my first managerial position right after finishing business school; since I was relatively younger than my team, I worked extra hard to earn their respect by making sure I looked put together each day," says Brittany Wise. "I didn't need to go out and buy a new wardrobe, but I started paying more attention at creating outfits that were well-kept and not overly dressed. That meant I looked for more ready-to-wear, no-ironing-needed blouses, blazers and cardigans, long necklaces that work with almost everything and pants that fit my shape. Then, I bought a few options in each color as my budget allowed. It made getting ready so much easier in the mornings, plus gave me confidence that I looked put together. The most important thing to keep in mind was to make sure I still looked like a part of the team."

3. Leveling up is important.

"Early in my career, I was advised to dress for the job I wanted (i.e., my boss's position), not the job I had," says Anne Shoemaker, owner of an executive coaching business for women. "So, if I were a junior associate, I would dress like a senior associate; as a senior associate, I would dress like a vice president; and so on.  I always 'leveled-up' at least one position beyond my role. As my career has evolved, senior management has relaxed their attire, enjoying the privilege of a more casual wardrobe that includes jeans and soft-soled shoes. Dressing in a suit would position me as an outsider — not advisable.  Accordingly, I now dress casually in keeping with the owners of the company." 

4. Dress with respect for your position.

"I took on my role in August 2019 after spending a lot of time in assistant and coordinator positions,"says Rennay Marshall, the director of marketing and development for national nonprofit, the Dream Factory, Inc. "When I first accepted this job, one of the first things I did was improve my wardrobe. To me, dressing like a boss equates to dressing with a level of respect for your position. As the marketing and development director, at any given time I could come face to face with a donor, business owner, reporter or any variety of individuals. It's important to me to look like the person who should be representing our organization."

5. Rock an authentic but professional wardrobe.

"I can definitely testify to consciously dressing differently when I started to make a run for leadership roles and also start my own company," says Tephra Miriam. "I've had many conversations with women in power about work-appropriate wear for women. One argument is that why should we have to 'cover-up' in an effort to try and fit into a very male-dominated corporate America. At the end of the day, we just need to first know who we're dealing with and know consciously if we are breaking the 'rules' in terms of dress code. Dressing like a boss to me is finding an authentic but professional wardrobe that represents power and strength. In our current global workforce, I intersect with many different people from different backgrounds and it's to my benefit to dress in a way that is true to myself but also respectful of different global ways of doing business. For me, that's finding different styles that are uncommon and bright colors."

6. Dress in a way that exudes confidence.

"I have always been the only female C-suite executive since I was in my 20s, and I am a curvy woman and look young for my age, so I found myself struggling," says Elyse Kaye, founder and CEO of Bloom Bras. "Sweater sets made me look voluptuous. Wrap dresses felt like maternity wear, and suits drew conversation that I was interviewing. I tell every woman that I mentor that, while it is unfair and unjust, it is always better to dress in a way that exudes confidence. I have managed very large teams and worked with the top leadership at hundreds of companies. The last thing I want them talking about was my outfit."

7. Look like a leader.

"While our company culture is casual, I've found it's still important to up-level my look so that, while it still reflects my personality (quirky and fun), subconsciously I come off sophisticated, wise, professional and that I have a leadership quality about me in addition to a friend-type vibe," says Angela Bonnici, vice president of media at Superconnector Media.

8. How you dress is a reflection of the company you manage.

"I am most comfortable in blue jeans and cotton shirts;  however, soon after founding a nonprofit and being in the public eye, I recognized that I needed to change my style," says Jodi O'Donnell-Ames, founder of Hope Loves Company. "I began dressing like a boss because everything you do as a leader is a reflection of the company that you manage. I (reluctantly) put away my go-to jeans and purchased dress pants, dresses and suits. Then I got the heels to match. I think that it's important to look and feel the part when you are representing an organization and, although some may think that clothes are immaterial, how you dress does matter! When I dress like a boss, I feel that I am respected and heard."

9. Dress to be ready for anything.

"I recently took over as CEO of a dating app; I work remotely from my team most days as we are based in different states, but taking on this new role as the face of the brand challenged me to be ready to elevator pitch the company at any given time, sometimes literally in an elevator," says Christiana Yebra, CEO at Vouch. "I dress as if I might be photographed, interviewed or might even meet at investor each day!"

10. Dressing like a boss means freedom and vision.

"The phrase 'dress like a boss' means both freedom and vision to me," says Denesha Chambers, a licensed professional counselor and certified grief specialist in the suburbs of Atlanta, Georgia. "I recall attending a professional development conference for Professional Counselor entrepreneurs, just as I was starting my own business. The host, Casey T., advised us to 'Dress like the client you want to attract.' That advice has stuck with me and, to this day, I consider it whenever I am selecting my attire for the day. However, I genuinely believe that is is just as important to be authentic with myself and allow myself to be free to be me. Therefore, my boss style is 'casually chic.'  Prior to being a boss, I simply monitored my attire to the dress code and gave it very little thought."

How do you dress like a lady boss?

Dressing like a "lady boss" means dressing in a way that suggests leadership and authority. Many women in authoritative positions choose to level up their wardrobes in order to distinguish themselves as leaders in their workspaces. They may do this differently depending on the company culture so, while some lady bosses may wear power suits to work, others may dress up by wearing slacks over jeans. The important thing to remember is that how you dress doesn't make you a boss but, for better or worse, it can impact the way others perceive you.

What do female CEOS wear?

Female CEOs wear a variety of different clothes depending on their workplace cultures. Some women in leadership roles may wear suits and dresses to the office with high heels every day, which is especially true in the corporate world. Meanwhile, other female CEOs, especially in more startup cultures, may tend to wear jeans and sneakers. And, of course, others meet in the middle with slacks and blouses or sweaters. In other words, female CEOs dress to fit the company culture and, while some choose to distinguish themselves apart from the rest, others choose to blend in.

What should a manager wear?

A manager should wear whatever makes them feel comfortable and confident enough to do their job well. This typically means dressing to fit in with the company culture so that they feel like they're representative of the company and its values. Of course, managers are still people with individual tastes and styles and, therefore, they're entitled to show personality in how they dress, too. Many choose to do with fun colors, prints and/or accessories.

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AnnaMarie Houlis is a feminist, a freelance journalist and an adventure aficionado with an affinity for impulsive solo travel. She spends her days writing about women’s empowerment from around the world. You can follow her work on her blog, HerReport.org, and follow her journeys on Instagram @her_report, Twitter @herreport and Facebook.

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