“Dress for the job you want” is an oft-repeated adage, and excellent advice at that. After all, looking the part = playing the part = reaching a mindset where you don’t need to pretend anymore. There is, however, far less colloquial wisdom out there about dressing for a dream job you already have and love. This can be a trickier challenge to take on when your career is quite busy, and there’s precious little time to think about the message any given outfit conveys.
But it does pay off to put thought into a work wardrobe, especially for women in a position of leadership. The right look can project confidence and competence — think a perfectly fit suit in a C-suite situation, a striking jumpsuit and heels for pitching a creative project, or just the right relaxed trouser jeans and button-down shirt for taking a casual coffee meeting. It’s such a simple way to take a little pressure off any professional situation: By wearing clothes that reflect your place in a particular field, you feel more secure in your position and authority. (Because yes, even the most successful amongst us get imposter syndrome — and, also yes, fashion can help counteract it.)
This mindset has certainly held true for the seven trailblazers and power players below, all of whom have learned how to harness style to support their goals across a wide range of industries. Keep scrolling for more on what they wear day-to-day, and for their milestone career moments.
Helen Aboah, COO of Atelier Jolie
How does personal style play into your job?
My role requires balancing strategic and operational planning with collaboration across diverse creative mediums. Fashion and art are central to our work, and how I present myself reflects our brand’s mission. My go-to outfit is a black Atelier Jolie blazer with three interchangeable collars and custom patches by artist Duke Riley; it’s as adaptable as my schedule. Paired with Another Tomorrow tailored trousers and a silk blouse or Urban Zen cashmere sweater, the look feels polished, genuine, and flexible.
How has your look changed since moving into a leadership position?
I’ve led a diverse range of brands from Alexander Wang to Donna Karan and have always believed in incorporating each one’s unique DNA into my style, which is why I’ve worn nearly all black throughout my career. Early on, my style was functional: I dressed to let my contributions to be the focus, rather than my attire. Atelier Jolie’s spirit of boundless creativity and personal expression resonates deeply with me. Now, with a packed schedule that involves everything from board meetings to creative collaborations, I value a wardrobe that can transform with the right details and that means. I’m someone who likes to bring fresh touches to my look — such as a handbag from Esha Soni, knitwear from Diotima, or really everything from Junya Wantanbe and A.W.A.K.E Mode — that add sophistication and intention.
Describe an outfit you wore for one of your most important professional moments.
The two most significant moments in my career were tied: opening Atelier Jolie’s flagship location and launching my private equity firm. For both occasions, I wore the same outfit, an Atelier Jolie coat, black trousers, and a black blouse, accented with gold jewelry to capture the celebratory spirit of each day.
Jamie Gersch, CMO of Rothy’s
How does personal style play into your job?
Having worked in the casual apparel space for years, my style leans in that direction: a great cashmere sweater in winter, a relaxed dress in summer, and lots of denim year round. I’m lucky to be the CMO of Rothy’s, where I get to use our incredible shoes as the foundation of most of my outfits. Whether it’s our clogs (I hate to admit it, but I now own five pairs!) or the new Cap Toe Mary Jane, I love starting my day by picking the shoe that fits the occasion.
How has your look changed since moving into a leadership position?
I’ve stayed true to my personal style as I’ve grown into leadership. Rather than changing my overall look, I’ve added pieces that allow me to dress up when needed — including a variety of blazers, dresses, and polished outfits.
Describe an outfit you wore for one of your most important professional moments.
I’ve been lucky to experience many memorable professional moments, but a recent highlight was opening our Fifth Avenue flagship in the heart of NYC. It was July — peak summer — so I planned around the weather, wearing one of my all-time favorite dresses from Apiece Apart and pairing it with our black Weekend Slide sandal.
Cassandra Welchlin, Executive Director of the Mississippi Black Women’s Roundtable
How does personal style play into your job?
I am a fashionista at heart and love dripping in style. It’s part of my brand: I grew up in a household that taught me that I represent the family at all times, and therefore how we presented ourselves was important. I learned how you look says a lot about your character and, ultimately, how people will treat you. I grew up watching my mom put on stylish clothes and her daughters matched her. My father is a bit of a diva himself — he likes nothing but the finest. I’ve often been told that I have presence when I walk into a room and people pay attention. I use that to my advantage to move the work forward. My go-to-work outfit most days usually includes a statement piece. I always wear color — and I always wear heels.
Has your look changed since moving into a leadership position?
No, I always show up as a fashionista, regardless of if I am working for myself or someone else. I can be at home working and I will still put on my finest. I like walking with purpose and fashion helps give me confidence, poise, and power.
Describe an outfit you wore for one of your most important professional moments.
I spoke on a high-profile panel discussion in Jackson last November. It was for The Atlantic, one of the nation’s most influential news magazines. I remember thinking I had to show up looking the part, to let folks know that Jackson is no slouch in the fashion department. So I wore a cobalt blue leather dress with a houndstooth wrap cape and hot pink shoes. My earrings had all the hot colors in them (blue, fuchsia, red), which really helped tie the outfit together. I don’t know what I got more compliments on: my speech or my look!
Lyndie Benson, Founder, Chief Creative Officer & CEO of Bleusalt
How does personal style play into your job?
I founded Bleusalt with the intention of creating classics items for anyone to curate an elevated wardrobe around, and I’ve always dressed in an elevated yet comfortable way no matter the situation. If I’m dressing day to night, for example, I’d wear a classic basic top like our Luxe Blazer, Classic Crew, or Classic Button Up with a pair of trousers or skirt in neutral tones.
How has your look changed since moving into a leadership position?
Before starting Bleusalt, I was married to a touring musician which taught me to pack light. I was always traveling but still needed to look quite put together. It taught me how to curate capsule wardrobes for ease of dressing and packing. Opening up your closet to find every piece working together is the dream, and this approach to dressing inspired Bleusalt’s line. I believe that being comfortable while looking elevated can bring out your confidence so that you are able to focus on the tasks at hand and be free of thinking about your clothes.
Describe an outfit you wore for one of your most important professional moments.
My most important professional events have been when I’ve represented my brand on camera. I always love a polished, classic look that features a mix of Bleusalt pieces that blend luxury and sophistication. Usually I choose neutral tones, but I do enjoy a pop of color every now and then. I start with a silhouette that works best for me and the situation and mix form-fitting pieces with oversized ones. So if you have a sleek bottom, I might suggest wearing a voluminous top and blazer. The same goes for a fitted top — I’d pair it with an oversized or flared bottom.
Roanne Adams, Executive Creative Director of RoAndCo
How does personal style play into your job?
At my creative agency RoAndCo, we work with brands across fashion, beauty, wellness, and tech. I started my career as a graphic designer working with fashion brands and for fashion publications, so style has always influenced my work and vice versa. For work, I lean minimalist in my clothing choices and love supporting female designers, especially those I know personally or have worked with. My go-to work outfit is a bit like a uniform: blazer or button-down & pants (usually from Apiece Apart, Rachel Comey, or Chava Studio), jewelry by Sophie Buhai, and a red lip.
How has your look changed since moving into a leadership position?
I’ve owned my agency for 18 years, so my style has remained consistent in the sense that I always aspire to look put together. But it has evolved over time. In NYC, where I attend in-person client meetings, I wear boots, structured blazers, and often paired with a trench coat. In LA, I prefer looser clothes and slides.
Describe an outfit you wore for one of your most important professional moments.
For the launch of my magazine, Romance Journal Issue 3, at the Proper Hotel in LA, I wore a plum maxi dress by Ulla Johnson (a former client), paired with my favorite Rachel Comey jacket, belt, earrings, and maroon patent leather clogs.
Erin Allweiss, Founder Of The No.29
How does personal style play into your job?
The No. 29. is a PR agency where we represent people, brands, and technologies that are making a positive impact on the world, which includes a deep focus on sustainable fashion. Because we work across so many industries, I need my outfits to translate for fashion spaces, but also land in political and sustainability circles. And since I have a lot of evening engagements, I’ll often do a quick change at the office. My go-to work outfit these days is almost always a pair of Rachel Comey shoes (I live in these, though I’m coveting these Toteme shoes), a Maria McManus skirt or blazer, a Baserange top or dress (also their bras and underwear), and a Lindquist Faba Bag (which also serves as a belt).
How has your look changed since moving into a leadership position?
When I worked on Capitol Hill, I had to adapt to political dressing and — as someone who loved fashion — tone things down. Mind you, this was 2005-2010, and Michelle Obama really made it more acceptable to embrace personal, expressive style. I was also lucky to work for a member of Congress who was more progressive in every sense of the word. While I started off wearing only suits, the office let me do what I wanted. I was able to find ways to play with color and accessories. This won’t sound edgy at all today, but I was layering and belting cardigans over dresses and skirts I’d find at New York consignment shops. I think the fact that this was innovative speaks to the specific limitations of DC dressing.
Describe an outfit you wore for one of your most important professional moments.
I remember wearing a black Theory suit and Jimmy Choo heels (bought at a consignment shop) to my first interview on Capitol Hill. It was for a job working as the communications director for Congressman Earl Blumenauer (Portland, OR). I wanted the role so badly, but was 24 years old, had total imposter syndrome, and never thought they’d hire me. So I wanted to feel armed walking into Congress, which was quite intimidating. I ultimately got the job, which was the most important start to my career. I don’t know if it was the suit, but 15 years later I still remember getting dressed for that big day.
Sheena Meade, CEO of The Clean Slate Initiative
How does personal style play into your job?
The Clean Slate Initiative is a national, bipartisan organization working to advance policy that clears eligible arrest and conviction records. I sit with many other CEOs and that does play a part into how I show up when I have to be around the table with other leaders, especially in different sectors. I meet with people in the business sector, venture capital, our donor community, philanthropists — and so sometimes I may lean into more of a conservative look. But my go-to work outfit most days involves cute, easy slides because I’m on Zoom meetings and nobody sees my feet.
How has your look changed since moving into a leadership position?
I bring the style that I rock in my personal life into my workspace. As women or CEOs, sometimes we feel like we have to fit a mold, but I think it’s OK to lean into your femininity and have fun with your look. It doesn’t have to be all seriousness and pant suits all the time (but if that’s what you’re most comfortable in, then rock it!). I like wearing my big pumps with a tailored dress with a long zipper in the back; other times I like wearing a nice dress with some fashionable sneakers, especially because I’m running through airports all the time. I try to bring some swagger to my profession, especially when I’m out speaking.
Describe an outfit you wore for one of your most important professional moments.
The most important professional moment in my life was delivering a TED Talk to a live audience of almost two thousand people. I wanted to make sure that my outfit would demand their attention. The look wound up being a three-piece purple suit, with a pink blouse to add a pop. Purple represents royalty, resistance, resilience. It also signifies the bipartisanship of the work that we do. We don’t just work with people in red states or blue states, but we bring people together. When you combine red and blue, it makes purple.
