5 Fashion Items CEOs Wear to Feel Confident as Hell

Here at Who What Wear, we believe in the power of clothing. There's a reason we always put on our favorite shirt for an important meeting or reserve that one cocktail dress for special occasions. It's because when we wear these pieces, we feel most comfortable in our own skin and most equipped to take on whatever life throws at us that day. Whether you're giving a big presentation or interviewing for your dream job, what you wear can transform the way you feel and, ultimately, carry yourself.

To find out what other women wear to feel most confident, we chatted with CEOs from companies like Good American and CultureBanx who have achieved remarkable success in their fields. Whether it be a blouse in a bold color, an elevated pair of heels, or a power suit, these are the best work clothes that successful women swear by for next-level confidence in and out of the office. Ready for some empowering outfit inspiration?

Briefly describe your job and what a given day might entail.

"Being the CEO and co-founder of Good American means that no two days are ever the same! I'm as involved in the business side as I am in production and design to ensure that each part of the company is cohesive and aligned with our mission. When I'm not traveling for work, you'll find me in the office at meetings with the various department heads at Good American. I'll brief the design team on new concepts for the upcoming season, and I'll even test out the products for myself throughout the day to verify each new fabric or design is functional as well as stylish."

Which fashion item(s) do you wear when you want to feel most confident at work, and why?

"I'm currently wearing Good American's new collection of dresses. Our dresses are super comfortable, versatile, and perfect for taking me from daytime meetings to post-work dinners. Throw on a pair of heels or sneakers, and you have two completely different looks that make you feel confident no matter the occasion. Plus, I’m always in a pair of GA jeans. I mean, they make your butt look amazing, and that sparks confidence. How could I not wear them constantly?"

Shop versatile dresses for work and beyond:

Briefly describe your job and what a given day might entail.

I'm the CEO of CultureBanx, a media company that creates business news for hip-hop culture! Creating the future of woke business news entails early mornings, late nights, and lots of music to stay at the forefront of great content. Typically, I'm racing through NYC between different meetings as I evangelize on behalf of the business to investors and clients alike to continue building an insightful and entertaining media brand.

Which fashion item(s) do you wear when you want to feel most confident at work, and why?

I feel most confident with minimal accessories and brightly hued outfits, preferably with an awesome pattern. Since I have a big personality I need my wardrobe to also speak volumes as well. Due to my never-ending travel around Manhattan, I usually wear a fantastic pair of nude flats from Rebecca Allen that I can easily fit into my uptown style, or that can be more causal to complement my downtown swag.

Shop pieces in bright colors and bold prints:

Briefly describe your job and what a given day might entail.

I'm the co-founder and creative director of The Daily Edited. My working day generally starts quite early (before I go to Spin); as soon as I wake up, I check and respond to emails that I have received overnight from our U.S. team (I'm based in Sydney). I then go to Spin and breakfast and then get to the office at around 10 a.m. where I usually start the day with administrative work for the business that is not too interesting, going through sales reports, reviewing draft EDMs, responding to my team on operational matters, reviewing the merchandising across our stores and in our online store. I then will have from 11 a.m. to 1 p.m. open for phone calls, face-to-face meetings with anyone who needs to see me, etc. After lunch, I then get into my "creative" work when I think about the product, imagery (yes I produce 90% of the shots you see on the @thedailyedited social channels, campaigns, marketing strategy, etc. I would then end the day with catching up on whatever has come up during the day in the business from any customer service, staffing, or inventory issue.

Which fashion item(s) do you wear when you want to feel most confident at work, and why?

I do love to wear a suit, however, nothing too tailored. I have some oversize blazers from Celine I love to wear with a tapered trouser. I just feel put together and organized when I'm in a matching set, which helps me execute my very ad hoc workflow.

Shop suits:

Briefly describe your job and what a given day might entail.

My job is CEO of Warp+Weft, an inclusive, sustainable, and affordable denim. Being the leader of such a mission-driven company and passionate team is the ultimate highlight of my life, and I try to live every day as positively as I can. In order to do that, I have to have a routine when it comes to my sleep, exercise, what I eat, and how I dress. I find that having uniformity with those things in my life helps me focus on my work and other activities. During the workweek, I wake up around 5:30 a.m., spend about two hours reading, centering myself, and listening to podcasts. Then around 7 a.m., I exercise (I've found any type of cardio works for me). Around 9 a.m. I have a breakfast of eggs, broth, and a super-green smoothie. I do emails until about 11 a.m. and then head to the office for meetings with the team. I usually end the day around 6 p.m. It's very hard for me to socialize during the week because I like to be in bed by 9 p.m. Weekends are a different story!

Which fashion item(s) do you wear when you want to feel most confident at work, and why?

Like most people, I couldn't be bothered with what I wear to work but need and like to look put-together. My work uniform is usually a T-shirt and our CDG vintage straight-leg jeans in the summer and the same thing plus a leather jacket in the cooler months. I'm not very experimental with my workwear, and my style really hasn't changed over the years. I have the same jean fit in four washes, and my trick is tone on tone—white jeans with white T-shirts, black with black and so forth. It looks chic plus it's super comfortable. I'm also a real Canadian tuxedo girl.

Shop classic straight-leg jeans:

Briefly describe your job and what a given day might entail.

I am the co-founder of Year of Ours. No day is the same, but something that is usually consistent is a morning workout. Once the workday starts, I am usually balancing our design, sales, and marketing teams from our L.A. factory or showroom unless I am on tour with the brand visiting clients or hosting pop-ups. 

Which fashion item(s) do you wear when you want to feel most confident at work, and why?

I am usually living in leggings and sneakers, so if we have important meetings with buyers or media or a big event, I usually try to swap out my Nike’s for a heel or elevated sandal and a blazer. I add some jewelry, a bit more makeup, and I feel like I can handle anything.

Shop elevated heels:

Next, see the nine outfits our editors are wearing to the office right now.