I Was Told the Only Cashmere I Owned Looked Like a Sweatshirt
What we wear to work costs more than money
When you’re on deadline as a reporter, your only focus is the clock. The minutes you have left to file your story. So when my boss came up behind me at my desk, where I was focused on the words, I didn’t think anything of it.
It wasn’t uncommon for him to come stand behind me and read over my shoulder, waiting for me to finish.
“What are you wearing?” he asked, lifting the hood on the back of my navy cashmere zip-up sweater. Polo Ralph Lauren, with dress pants. It was one of the nicest clothing items I owned at the time, and I still was carrying a balance on my credit card because of that purchase.
“Why are you wearing a sweatshirt to work? That’s unprofessional. Don’t do it again.”
It would have been better with buttons — I understand that now. But it was cashmere, from an actual brand, and I thought I’d done something right — finally — when it came to my work appearance.
I never wore it again and donated it shortly after.
That was more than twenty years ago. Only now, cautiously, am I starting to consider cashmere again. It would have been great if that was a teachable moment that somehow allowed me to morph into someone capable of dressing inconspicuously, blending in with the rest. But it didn’t. It was embarrassing, done in front of others and continues to be why I have apprehension about what I wear to work.
The data, at least, confirms I’m not suffering alone. Compared to men, women have more stress about their work wardrobe. Fashion feels like it ignores us, and it’s impossible to find a pair of pants that fit from one week to the next. We don’t want to look like a frumpy grandma, but we’re also probably not putting our midriff on display at the office coffee bar.
As we hit middle age, our mind and body morph with change. What do we do with this discomfort? We shop. It isn’t because we’ve figured it out. It’s because we haven’t! We’re buying more clothes, trying to find a fit we’re ok with. In fact, women 45 to 54 spend more on clothing than any other age group. Hello Retail Therapy.
Over the years, I keep getting my work wardrobe wrong: I have the stories and outfits to prove it.
My mother tells me “suits are so in,” even though I didn’t ask her for advice. My father tells me “dress like your mother. She always looks so nice.” Again, I didn’t ask. And neither work in corporate.
I’m embarrassed to tell you how old I was when I stopped allowing my mother to go shopping with me. Let’s just say I already owned my first home. And even then, I needed a therapist to help me push my mother out of my closet.
While necessary, I still haven’t gotten it “right.” I lost out on a contracting role because “clearly she doesn’t understand our culture.” They didn’t like what I wore.
I actually hired a stylist who I paid good money to and bought clothes she suggested. She wanted to lay out what I would wear and take photos. I was then supposed to follow the photos as she said. Just because she could wear pointy toe boots all day didn’t mean they felt good on my feet. Nearly everything I bought with her I’ve since donated. I simply couldn’t do it.
A business coach hired by the company I was working for at the time was there to deliver what I hoped would be real insight to my challenges in corporate. Hence the paid-for coaching.
“Just stop wearing the Hello Kitty socks to work,” I was told.
I was wearing a pantsuit for a big meeting where I was presenting. Preparations had been obsessive and underway for months. I was desperate to get it right. You couldn’t see the socks. And did I mention I wore a suit?
It’s taken me years to understand the Hello Kitty socks weren’t the problem. I was.
That the way I talk to people can come across as hurtful, even counterproductive. It’s been hard to accept because that isn’t the person I want to be. I want to communicate in a way that empowers others to also have their voice. So we can work together. But I now understand that too often my approach was divisive, even cruel. And I hate that.
It’s been extremely challenging to understand and accept and it has taken years of work to evolve. I won’t go so far as to say it’s fixed, but it is a work in progress.
Very few people have ever shared their honest experience of me. Instead of telling me the hard truth, they focused on my appearance.
Luckily, the coach became a friend and now we can laugh about the Hello Kitty socks. But first she had to fire me as a client.
I’m now considering cashmere again. Not because I understand what the proper work uniform is for a middle-aged woman in a corporate job. But I do know I want a luscious cashmere pullover with a v-neck, so a shirt underneath can peek out. And believe it or not, I actually want it in navy again. Is that progress or regression? I’m not sure I care.
Join Our Live Video Chat Thursday April 2 @ 4:45 pm EST / 1:45 pm PST
Even though many of us are suffering, silently, nothing has made it any easier. Our challenges with work wear haven’t been solved. What I want to know is: Why aren’t we talking about this with each other?
Join Amy Benavides and me to discuss:
Our Appearance: When It Helps Us Fit In vs. Stand Out
Thursday April 2 @ 4:45 pm EST / 1:45 pm PST
Amy is an expert on spies — how cool is that?! Of course all I think of are the incredible designer duds featured on Killing Eve. Amy sets us straight on how someone really dresses when they’re undercover.
Check out Amy’s read and plan to join us for the conversation. We’d love for you to share your story with work clothes, ask questions, teach me what I’m doing wrong! We’re here for it all. See you Thursday.








What a great piece! It is true that people point out perceived issues in clothing instead of addressing an issue that is harder to discuss. I also think it's interesting that men will complain that women "get to wear whatever they want" but they don't understand the issues we face. Clothing styles (pointy vs rounded vs square toe shoes, for example) change for women, as well as our body changing throughout the month.
I look forward to our discussion.