Do I Have to Wear a Dress For Success?
How to dress for yourself and be professional in the workplace.
When I was in the 6th grade I was a tomboy. I lived for playing football and kickball at recess. I had zero understanding of what the gaggle of girls (wearing tight Jordache jeans) was doing as they sat in circles on the playground, singing AC/DC songs and gossiping about boys.
Yes, I’m aware there is a lot to unpack in that sentence.
At the time, I had a lovely and very cool teacher, Mrs. Cincotta. After one particularly sweaty recess, she pulled me aside for a heart-to-heart. She told me that I had to figure out how to fit in with the girls because change was a comin’. She was of course talking about puberty and all the gendering and separating that happens with preteens. There may be less of that today, but as a mom of two kids in this age bracket, I can attest it’s still a thing.
In our little chat, Mrs. Cincotta offered me a dollar for every day I wore a dress.
The proposition intrigued me. A buck a day was big money to an 11-year-old in the 80s. But I couldn’t do it–even for that kind of money. Wearing dresses was not who I was. It’s still not. Though I’ll pop one of those bad boys on for a wedding or a commercial audition if required. Even then, I feel almost like I’m in drag.
When I look back on that moment, I have love for the teacher who tried her best to help a young kid have an easier go of an awkward stage of development. Make no mistake, she was right. My time in middle school and high school was hard for all the reasons her spidey sense picked up on. Hello, young, lesbian Robin. I see you!
But that moment is also important because it was the first time I was forced to consider other people’s expectations of who I am and how I look versus my need to feel like myself, to feel okay in my own skin. Confronted with the buck-a-dress proposal, I had to decide what I was willing to lose in order to be me.
This question of what people think about how we present ourselves doesn’t go away as we get older. It’s particularly present in the workplace. At the office, we walk a tightrope between bending to the will of corporate culture and dressing to make ourselves feel comfortable or like ourselves.
I delved into this topic on Season 1 of my podcast Well…Adjusting. I chatted with Larkin, a 20-something in the interior design field. She came onto the show to ask how to dress for success, but also how to dress for her queerness and still be taken seriously at work. We picked apart this question in great detail. So much detail that we needed several cocktails, and you can hear the ice machine working overtime in the middle of the episode. That’s some real in-depth chat.
The result– we unearth larger, connected questions about imposter syndrome and taking up space in the office as a woman.
Luckily we had an expert on hand to talk about how to dress in a way that enhances you, and enhances your career. We also talk about how to be a boss bish in the workplace. Here’s Kerry Sullivan sharing some of her wisdom from her 20-plus years of experience as an executive at fortune 500 companies like Nike.
Kerry:
I was in the fashion business, and when I came from New York I was overdressed and I freaked people out. I was wearing suits and I had a clipboard and I didn't fit in. I had to learn how to dress casually. And that's the advice I give. Try to move into how you feel comfortable.
I had one woman that worked on my team, she wore a long black skirt every day. But then she would put a denim jacket on or put on a leather jacket or a different blazer. She would change it up with a t-shirt, boots, or heels. But she always had that signature black skirt that I thought was genius. I was envious because she looked so comfortable. It's like the Rachel Maddow suit. She wears very simple makeup, no jewelry, and no static, so then her voice is heard. It simplifies things. Then people hear you.
In your work environment, you can take that cue from other people around you. It's something to observe in coworkers. Think, “Who do I idolize in my office?” Everybody has an office crush or is intrigued by somebody. Think about what is it about them that you’re attracted to. Are they commanding the room? Are they confident?
And remember, you will get advice from all sorts of people, but only you can listen to your belly. You have to connect to your own wisdom and breathe into that. You have to meditate on yourself because if thinking about wardrobe and how you’re perceived is possessing your time, that’s static in your everyday conversation with yourself. That's negative talk. You have to quiet that talk, and think, “Do I want people to hear me or do I want people to see me?” Some people that are seen are bags of bullshit. They look awesome, and they're cool, but they don't know what they're talking about. They don't have respect because their words are wishy-washy or they're not subject matter experts,
It's good to have a little mantra. “Today, I'm going to be confident. I'm going to be open. I'm going to be positive. I'm going to listen to what people say before I judge what they're saying.”
And give yourself time. It's not an overnight thing. A nice suit is not gonna solve your woes. Bleaching your hair is not going to help you deal with an asshat in your office.
I think self-possession is the key.
It's hard being a female in a workplace. The pressure on women has always been there. When you're presenting, that's when the nerves go through the roof because you know everybody's critiquing you from your eyelash to your eyebrows to your shoes to how you're carrying yourself. So, to get through that, center yourself. Remember, “I have subject matter expertise, and they're here to listen to what I have to say.”
Why not give yourself that?
Want to hear more of this chat? Want more Life Hacks and more Well…Adjusting?
Listen to Well…Adjusting now. It’s available at https://pod.link/welladjusting or on your favorite podcast platform. And don’t be afraid to follow, rate and review too. While you’re at it. Oh, and season 2 of Well…Adjusting drops Tuesday, March 21st.
Get ready