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5 Different Women on Getting Dressed for Work

What a reporter, consultant, project manager, and more wear to feel confident, comfortable, and powerful.

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A woman sitting at a work desk Photo: Morsa Images/Getty Images

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Shopping for work clothes isn’t easy. Fit and budget matter, as does style, but that’s certainly not everything that goes into getting dressed in the morning. Finding clothes that make sense in a particular work environment, or that are office-appropriate but still comfortable, isn’t the easiest feat. (Is it any wonder that many of us get a little stressed out on Sunday nights?)

We spoke with five women who work in different fields and are at different stages of their careers about how they dress for work, and specifically what they wear to feel in charge, respected, confident, and focused.

Julia Craven, 24, civil rights reporter at The Huffington Post, Washington, DC

What she wore on her first day at work: My first day at HuffPost, I remember freaking out about what to wear. It’s a pretty casual office, as far as dress goes. I was still really nervous, because as a young black woman, I’m like, I have to do everything right. My hair has to be right, my outfit has to be right. I felt compelled to look as professional as I could. I always have this voice in the back of my head: “You have to do everything right because this is the society we operate in.”

What she wore to cover the 2015 State of the Union, given by President Obama: I remember leaving the office and taking my first paycheck and going to the Macy’s over in Metro Center to find some dress pants that fit and weren’t too tight. It was really stressful. I was all by myself, I was scared to ask any of the salespeople for help, and I was interning with two guys who already had really nice business clothes. They were ready — they were prepared.

Eventually I did find a nice black pair. I think as I’ve gotten older, it’s gotten easier. I don’t have to go to Macy’s, or if I do, I know exactly where to go. I can go to Express, or I can order something.

Where she buys casual work clothes: If I’m meeting a source at a coffee shop, I’ll just throw on some black pants or jeans — something nice and sleek-looking — and a nice shirt. If it’s a source I’ve been working with for a while, I’ll just throw on some leggings and some sneakers, and often that person also doesn’t dress up. I’ve been in situations covering a protest and I have on leggings and sneakers and a T-shirt that probably has a saying on it, and I’m running around and I’m talking to all of these people, and I feel so confident in my reporting because I’m comfortable.

Have you ever heard of Girlfriend Collective? Those black leggings that look like pants — I live in those. They’re comfortable, they look like straight-legged black pants, and if I’m going to a business-casual event and I can pull them off with a nice shirt and a good shoe, that’s definitely my go-to.

Rachel Schallom, 28, newsroom project manager at The Wall Street Journal, New York

Being taken seriously at work: I was promoted to management pretty early in my career. I’ve always worked in digital, and getting newsrooms to be more digital has always been really hard. And what I’ve found was, when you’re telling someone that they need to change the way they do something, and you’re not only a woman but a very young woman, that doesn’t always go so well. I’ve noticed a big difference in the respect that I got based on what I wore.

How she dresses for the newsroom: Journalism is a fairly casual industry. I often wear ankle pants from Old Navy that I have in six different colors. I pair them with some sort of blouse and a blazer. I used to wear lots of cardigans, but in the past two years, I’ve moved into the blazer movement.

I probably bought eight different blazers in different colors. I feel like that makes me look professional but not overly dressy for the newsroom. When I wear really dressy things, people are like, “Do you have a date? What are you doing?”

I’m also super conservative about the length of my skirts and dresses for work. I would wear dresses, but if they were even close in my mind to being too short, I felt uncomfortable. A lot of my work is having hard conversations and dealing with hard problems, and I can’t also be doing that and having confidence issues.

Cyndie Spiegel, 39, small-business consultant and founder of The Collective (of Us), Brooklyn

What she wears to meetings: If it’s in the fall, I rely on cowboy boots, no matter what, because I can dress them up or dress them down, and if it’s in the summertime, I have a cashmere pashmina or a denim jacket. I worked in fashion for 15 years, so there are a ton of accessories, no matter what I’m wearing. Ten bracelets, earrings, a necklace.

When I worked in [the fashion industry], I worked in luxury, and it was different. You have to dress in designer clothing all the time. You have to look the part and sort of play the part. So, I would wear blazers with jeans, I would wear skinny pants and heels, or change into heels when I got to work. When I started my own business, I decided I wasn’t doing that shit anymore.

I still carry a nice handbag, but nine out of 10 times, I run out of the house with a tote. If I’m going to a meeting, I’ll carry something nicer, but if it’s just around the neighborhood, I carry a canvas tote everywhere.

About those cowboy boots: I have six pairs of cowboy boots, and I always get them vintage. I buy them in vintage shops across the country, and one of my favorite shops is in Salt Lake City, and it’s called Decades. I’ve gotten probably three pairs from Decades.

The last fashion brand I was in, everybody else was wearing 4-inch heels, and I was a consultant for them for a few years and I wore my cowboy boots. It was one of those New York showrooms, so the designer stops in the middle of a meeting and says, “Cyndie. Could you stop wearing cowboy boots?” Which is just crazytown. I just literally looked at him and said, “You could just hire another director of product.” I could kind of see his mouth drop because no one says things like that to him.

Her advice to younger women, especially in fashion: Check in with yourself, and if you find that you’re wearing things that you don’t necessarily feel comfortable in, then ask yourself why and do something about it. You can be mindful of it and make sure that doesn’t happen again, [otherwise] you’re essentially pulling yourself further and further away from yourself.

Michelle Trombetta, 42, director of product management and user experience at Code42, a software company in Minneapolis

What she wears in a dressed-up office: I’m definitely a pantsuit woman. Especially in [the formal officewear] phase of my life, I had my men. I rocked Calvin Klein, Michael Kors. Those are the gentlemen who dressed me. Suits can be a little bit boring, especially if you’re curvier and tall. I always tried to dress it up either with a funky pair of brightly colored pumps or a pair of brightly colored flats. Or a statement necklace that would set me apart from everybody else.

On suits: One of the first bits of advice I got straight out of college, working for a consulting company, was if you wanted to be taken seriously as a woman in this business, you’ve got to be wearing a suit. It was a female partner in the organization, one of the few, and I definitely carried that with me for a long time. Even if I wasn’t wearing a suit, I was definitely better dressed than most of my peers and counterparts.

While I was interviewing, I wore suits. That’s who I am, that’s what I do. I feel strong in a suit. When I had my in-person interview at Code42, a software company where people wear hoodies and cargo shorts, I wore a red power suit. And, evidently, it was the talk of the entire office. I know why Hillary did it. It tells the world you mean business.

On a very retrograde dress code for women: In 1997, I started my job on June 1st, and June 1st was the first day at the company where women didn’t have to wear skirt suits. During the course of my training that summer, the trainers were having a hard time adjusting to women wearing pantsuits. They really wanted us to be wearing something of the same color, top and bottom. One of my colleagues and I went shopping, and I bought a lime-green suit, and she bought a berry-purple suit. Just completely obnoxious.

How she dresses at her current office: I’m pretty all over the place. I do feel like I command a room differently when I dress in more than jeans and a sweatshirt. I work in a casual environment; there are a lot of men in hoodies and cargo shorts. There are a lot of women in hoodies and cargo shorts. But as a leader in the organization, as well as who I am, I do feel like, in the words of Barney in How I Met Your Mother, I need to suit up.

Her advice for the next generation: I mentor a lot of women now. One of the struggles I’ve had in coaching them is: Clothes shouldn’t matter. And I know that. And as a second-wave feminist and what I went through, I feel like you either dress like the guys or you try to one-up the guys. Whereas the younger women, the third-generation feminists, are very much, “My clothes shouldn’t matter. It’s what I do.” In an absolutely idealistic world, it shouldn’t matter. But it does. You’re reflecting your personal brand. How we dress, how we carry ourselves, reflects our personal brand, whether we like it or not.

Liz Doerr, 32, director of engagement for a venture capital firm and a newly elected school board member in Richmond, Virginia

What she wears to work: I can kind of wear whatever I want as long as it looks smart, so no sweatpants or workout clothes. If I could go back to an era in fashion, it would be the ’70s — I love shift dresses and big prints. I have a long torso and I’m kind of narrow, so I like straight-line dresses. If I have to wear something nicer, I’ll wear a work dress and a blazer.

What she wore campaigning for office: I got a couple of nicer cotton dresses, and you have to wear comfortable shoes. Really, what I wanted to wear was workout clothes, because it was summer and it was super hot, but you want to wear something that makes you look somewhat presentable.

I love big necklaces and big accent jewelry, and I found, at least during campaign season, that wearing something simple — and accessorizing it — makes you somewhat memorable. I was campaigning one day, knocking on doors in the rain, and someone said, “Oh, I’m going to vote for you because you were wearing a really cute rain jacket and your Hunter rain boots!”

Her fashion philosophy: I believe in having a really good black work dress and also a really good pair of power flats. I believe in investing in those two items more than anything else.