“Glamorous teen mogul online, unassuming nerd in real life.” - The Star-Ledger
“You looked fat.” - a classmate after seeing me on CNBC
“Your hair is thinning. I guess your beauty is only in your brains.” - my former dentist
“You’re the goddess of the internet.” - my favorite myYearbook member
“You’re prettier than I thought you’d be.” - comment from multiple people I met at a conference
As the first friend request on myYearbook (and then MeetMe), my face was the first one millions of members saw. I was scrutinized constantly in messages and comments. It wasn’t limited to just the site or apps either; day traders on the Yahoo Finance message boards posted photos of me and added vile commentary when I was only twenty-one.
I developed a thick skin from a young age and learned to weather a constant barrage of comments on my appearance. I’m not alone. All women deal with consistent comments and pressures on their looks. Girls as young as seven feel pressure to be pretty. Throwing in the professional setting makes matters even more complicated.
I recently had lunch with a friend in her mid-thirties, whose colleague, in his mid-fifties, told her that she needed to dress “more professionally.” He missed her pencil skirts.
Her typical office attire consisted of dark jeans and sweaters–she was well within the stated dress code. She wasn’t the only woman asked to dress differently, either.
In her predominantly male workplace, no one says anything to the men about their dress. One guy has a habit of walking around in just socks.
She got a stylist, and though she does love her stylist, the comment on her attire is enraging.
There is pressure to “look the part” of an entrepreneur, a leader, a manager, a doctor, etc., but those expectations are everchanging. Instead, focus on these three things:
Be intentional
Though the clothes you wear have no bearing on your content, what you wear affects how you are perceived.
My friend’s calculation for what to wear depends on who she is meeting with. If it’s a tech company, jeans are okay. Bankers? She wears a suit. No one wants to be overdressed or underdressed, so you need to be intentional about what to wear in different environments.
In Mita Mallick’s Reimagine Inclusion, she recalls how she dressed a certain way at work to downplay her success because she was up for a promotion to which a friend agreed, sharing:
“Sure, we own nice things. We have earned them, and we don’t always need to wear them to work. Not the logo handbags, not the diamonds, and not those branded shoes. Don’t give them another reason not to pay us what we know we have earned and deserve.”
Similarly, the adage “dress for the job you want, not the job you have” exists for a reason. Though, this Business Insider piece explains it’s not that simple.
The most senior people at some companies may be the ones wearing flip-flops and hoodies because they have earned the credibility to wear whatever they want.
Before a job interview or event, seeing what fits within the norm makes sense. The reason isn’t to make the misogynist minority that prefers pencil skirts and heels happy—they are going to judge you no matter what.
The reason to be intentional is because it will help with the next step: dress for confidence.
Dress for confidence
What makes you feel most confident? Wear that.
At one conference, I walked onto the stage in three-inch heels—they may as well have been stilts. I looked like a newborn fawn learning to walk. I am not confident in heels. Other people may look and feel great in them, but if they hurt your confidence, they need to go.
Confidence is “the single most important differentiator in the workplace. It will be the person with high confidence and lower abilities who will get the job over the person with low confidence and higher abilities,” according to workplace coach and author Bonnie Low-Kramen.
Recently, I went shopping with my mom. I’ve always hated shopping, but she makes it easy. She has me wait in the dressing room with chocolate and brings me clothes to try on. I came into the store in my uniform of leggings and a T-shirt. Buying some new clothes made a huge difference in how I saw myself. Without a need to go into an office for about five years, I had forgotten how important it was to my mindset to feel confident in what I was wearing.
Similarly, a former colleague shared that she got dressed up when she had done video date nights on The League. She felt like it was more like a date and would be a better experience (unfortunately, most of the guys did not get the memo about looking their best). I would see similar comments from livestreamers. Though most livestreamers felt more attractive when they streamed, the people who got dressed up felt even more confident and positive about the experience.
Invest in figuring out what you like and makes you feel confident. For me, any outfit that subtly (or obviously) features animals in some way brings me joy. If you take pride in what you’re wearing you can be so much more confident in any setting, which also helps you ignore any stray comments.
Develop looks that you like at different levels of dress: casual, business casual, business professional, etc., so that you can eliminate guesswork and enjoy what you’re wearing. It’s much easier to feel your best when you look your best.
Stop commenting on people’s looks.
Years ago, I overheard a conversation between Bob, a man who owned a restaurant downstairs from my apartment, and an acquaintance of his.
Acquaintance: “Wow! You lost a lot of weight! You look great.”
Bob: “Yeah, I was very, very sick. I’m finally on the mend now.”
Acquaintance: “I’m sorry to hear that. Great side effect, though!”
Bob: (clearly annoyed) “I’m hoping to gain it back.”
It was incredibly awkward.
Don't comment on their appearance, especially with people you don’t know well. It’s the best way to avoid putting your foot in your mouth.
Similarly, if someone follows the appropriate dress code, keep your opinion to yourself. Heck, even if they aren’t in dress code, mind your own business.
Whoever you're talking to has likely already heard enough comments. Instead, listen to what they have to say.
Be intentional in choosing what to wear to feel more confident and bring your best self. Own how you look and what you wear. Developing that confidence makes a huge difference in ignoring the comments that don’t matter so that you can focus on the things that do.
Great read! I wrote sometime back about how confidence is key and your writing highlights why dressing the part by writing your own story is so integral to one’s confidence.