How Kerry O'Brien Founded Fashion's Favorite Underwear Brand With No Design Experience

"Sometimes people just stay on the path they're on because it's working out for them, and they're afraid if they do something else they may not be successful."
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Kerry O'Brien, founder and CEO of Commando. Photo: Courtesy of Commando

Kerry O'Brien, founder and CEO of Commando. Photo: Courtesy of Commando

In our long-running series "How I'm Making It," we talk to people making a living in the fashion and beauty industries about how they broke in and found success.

Kerry O'Brien, the founder and CEO of Commando, had never really considered working in fashion design, let alone in the lingerie market. She studied business communications at Waltham, Mass.'s Bentley College, landed internships with the likes of CNN and Senator George Mitchell and eventually took a job working in financial PR. Then, September 11, 2001 happened. The next day, O'Brien walked out of her office and away from her successful career as VP of Financial PR at Edelman.

"I did it at the time because, as part of my job, I read three to four newspapers a day. I had CNBC on all day long, and I just didn't want to relive September 11th over and over and over again," she explains. "When I look back in hindsight, the truth is I was burnt out and it was time for me to start a new chapter, and this just gave me permission. If you're good at something, that doesn't mean you're not going to be great at other things. Sometimes people just stay on the path they're on because it's working out for them, and they're afraid if they do something else they may not be successful."

O'Brien moved back home to Vermont to regroup. She had long felt like there was something missing in the underwear market, and she began to think she could fill that gap in women's lingerie drawers. Just a few years later, Commando was born. 

Today, Commando sells much more than seamless underwear, having branched out into categories like sleek bodysuits and comfortable-yet-stylish stretchy pants. It has also become one of fashion's favorite underwear brands, appearing across red carpets and runways season after season. O'Brien chatted with us to discuss how she built Commando into the powerhouse it is now, why the lingerie world is totally different than it was when she started and why having chapters in life is essential.

What first interested you in fashion?

Growing up, I always felt like I could do anything I wanted to do, be anything I wanted to be. I was kind of a dynamic young woman; I was a jock, but I was also a fashionista. I was the captain of the basketball team and the soccer team, and one of the things that you had to do was get dressed up when you went to away games, and I was always the one with the purple pumps and crazy yellow skirt, or something that was just super-fun for me. I always wanted to have one thing that I felt was unique about me, and I really used fashion as expression of that in the very beginning. 

The other thing I thought of: After September 11th, we had to leave our apartment in a big rush, and what do you do, what do you take? Most people would take pictures; I didn't have kids back then, so I grabbed my Prada techno pants and I ran out the door. You know you love fashion when you're like, "Oh my God, what's the one thing I can't live without? My Prada pants!"

A look from Commando. Photo: Courtesy of Commando

A look from Commando. Photo: Courtesy of Commando

What were you doing before you started Commando?

My last summer [of college], I got offered a job to intern at CNN here in New York. Then when I started, I got offered a job to work at "Nightline" during the nighttime, so instead of choosing, I did both. I don't like seeing opportunity go by, and if you're given an opportunity to work with some of the best people in an industry, you take the opportunity, even if it means that you're working twice as hard.

I did financial PR, which was perfect for me because I understood how a business was run, I understood how to read financial statements — which, by the way, everyone should learn how to read a financial statement, because it's not that. When you're financial PR, you're doing mergers and acquisitions, IPOs, earnings reports. You're dealing with Fortune 500 CEOs and positioning them, and they're all in different industries. I had everything from telecommunications to medical devices; I had some retail, but not that many. You learn to ask questions and be unafraid to learn about an industry, to really dig deep into each person's business, and that was a lifelong skill that helped me launch Commando. 

Why did you decide to launch Commando?

As the years went by, my love for fashion continued, and I had so many brands that I had an emotional connection to that I knew would never let me down. If I needed a pair of amazing shoes, I had a handful of designers that I know would not let me down; same with jeans and little black dresses. I did not have an underwear company that I thought really understood what I wanted in my top drawer, and that frustrated me. I felt like I was constantly sacrificing what I wanted to wear. 

I didn't understand why underwear was the first thing you put on your body, yet it was often the most uncomfortable and unflattering thing that you would put on your body. I wanted to change that, and I decided that I was going to see if I can come up with an underwear line that actually fit a woman's body, that was nice to it, that didn't have lines. If you have a line, it means it's digging into you, so not only is it unsightly under clothes, it doesn't feel that great on your body, and it certainly doesn't make you feel good about yourself. 

No one had really done this idea of doing underwear that had no elastic or trim; it's because I didn't know anything about it that I thought I could do it, because anybody that was trained would "know" that you couldn't do it.

What was that learning curve like?

I thought if I came up with an amazing underwear, that was going to be the hard part and the rest was going to be easy. I was really wrong. Trying to get someone to manufacture this garment for me was more challenging than I had anticipated, because I didn't have any contacts in the field. The people that I called wanted to know one thing: "How many units are you going to make a year?" I had no idea how many units I was going to sell a year; I was just hoping I was going to sell some! I went door-to-door selling it to boutiques, so it was not like I was already selling to major department stores, and because I didn't have a background, people questioned whether I would be successful or not. 

I am a big believer in asking, "If you can't help me, do you know someone else that can help me?" And along the way, I kept on asking people who they thought could help me. It turns out there were local sewers in the Vermont area; it was a group of Bosnian refugees. I went down to meet with them, and I said, "This is my idea, this is my prototype, can you help me?" and [the owner] says, "Kerry, my friend, we are in this together, I will be your manufacturing partner," and to this day, they have been. They're great to us. 

A look from Commando. Photo: Courtesy of Commando

A look from Commando. Photo: Courtesy of Commando

How do you decide what new categories to branch into?

My guiding post is what I want to wear and what I think would be amazing. We started with the top drawer — meaning underwear, bralettes, slips and hosiery — and we're moving down the drawers to everyday luxury basics. I always like to push the limits in terms of technology. When we first started, I only worked in microfiber, and no one thought I could do all the things I've done with cotton, but we continue to work across fabrications and styles and categories. 

I fit-test every garment, and I need to make sure that I love it and it works with my body. We fit-test all sizes; it's not just get one size and you grade it up and you grade it down. It's really wearing the items that you can make your luxury basics, like this top I'm wearing right now — I can dress this up, I can dress it down, you can wear it with jeans, you can wear it with a ballgown. It's one of those basics that you build your whole collection on. Commando is just a fantastic canvas for that.

How did the fashion and red carpet partnerships come about?

Just like so many other things at Commando, they are completely organic. It started happening somewhere around 10 years ago; designers would call us and say, "We love your underwear, it's the perfect foundation piece for our runway collection, the models wear it anyway. Is there any way we can work together for fashion week?" It started with a couple designers and then got bigger, and then a funny thing happened along the way. 

They started being styled visibly, so we get probably just as many calls for black high-rise panties to be shown as we do with nude tiny thongs. It's not just the designers and the stylists that are doing it this way — our consumers are styling underwear to be part of their looks, because there's no categories anymore. It's all part of your ready-to-wear look; it's what you're wearing underneath and deciding whether you're going to wear it visibly or invisibly.

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How have you seen the industry change since you started out?

So many celebrities from the very beginning have worn Commando, but it was almost inappropriate for us to talk about them wearing Commando underwear. Well, now, not only are they talking about it, they're showing it. She's mixing things up in a way that's completely liberating her, and there's no rules anymore for fashion.

I was at Raoul's in New York City, it was fashion week. We're waiting for a table, and I look across the room and there's this woman wearing a Commando slip for a dress. I went up to her and said, "Love your dress, who makes it? [Laughs] Don't worry, I know it's Commando." She's like, "I just feel so great every time I wear this slip so I wear it as a dress." Good! That's what you should do. That's one way things have changed is the whole attitude toward underwear and showing it and talking about it.

How has social media changed your business?

Our approach to business is to find the best fabrics in the world and put them in garments that we love to wear every day, and that will never change. What social media has done, though, is sometimes I'll create a garment and if it doesn't photograph really well, I might decide not to produce it. The whole visual element has become much more important.

It also goes back to fashion week; what I get out of it is inspiration to see how these talented designers are interpreting my underwear, and the same thing goes with all of our social media followers. Every day I get to see how people are interpreting things that I designed, and I find it enormously inspiring. 

Another thing that we have decided to do with the company, because I believe in authenticity and true partnerships, we don't pay for any influencer, at all. It's just off the table for us. 

A look from Commando. Photo: Courtesy of Commando

A look from Commando. Photo: Courtesy of Commando

What's something you wish you'd known before starting?

Nothing. It's been interesting; the mistakes were just as important as the successes, honestly. If you're not failing, you're failing. If you're not pushing yourself to the limit to fail, you will never reach your true potential and you'll never continue to move forward and innovate and create new and beautiful things. 

I always think it's going to be easier; when we come out with a new line, I'm thinking, "We've been doing this now for almost 15 years; it's going to be easier," but it never is. You're always going to have challenges, there are always going to be issues, there's always going to be setbacks along the way, and that's just part of it. You need to accept that that is part of the journey.

What do you look for in people that you hire to be part of your team?

Cultural fit is one of the most important things, because we have a very unique culture. We move very quickly at Commando and we demand a lot from people, and I don't mind when people make mistakes. I don't like it when people are afraid to make a decision because they're afraid to make a mistake. You have to look forward and look at where do we think fashion is going, where technology for fabrics is going.

What would you tell someone looking to start their own company?

I would say that it may seem like things were an overnight success, but there were a lot of sleepless nights along the way. It's hard, but it's worth it; if you feel you get stuck, ask for help, because I feel people like to help other people up. I feel like it's in our nature. When I feel stumped, I ask for help, and if they can't help me, I go to someone else.

Another thing is that you should always ask for more — you should ask for more from yourself, from your garments, from the people that work for you. Don't just say, "Okay, this is good enough." How can we make it even better, or how can I be a better business person or better designer? That is a never-ending process.

A look from Commando. Photo: Courtesy of Commando

A look from Commando. Photo: Courtesy of Commando

Something you've said is that you believe in chapters; why is that?

I think it's important that, directionally, people are moving forward. Whether you like it or not, there are chapters in your life; you may decide to get married and have children; you are going to get older; you probably will move at least once in your life. These are chapters in your life and sometimes you can decide to end one chapter and go to another. I think that the people who have the most success in their life is when they realize it's time to actually pick up the train and move it to a different track, and that is, in definition, turning the page, changing your chapter, purposefully. 

I started with two styles of underwear and two colors. Now we are in ready-to-wear. We can do anything we want to do within the Commando brand, and that makes me feel really great. I feel like there's no boundaries at all in our company, and this is my Commando chapter. There might be another chapter down the road, and that's okay! It doesn't scare me! In fact, I think it would be good.

So what would be your ultimate goal?

First of all, I think that Commando has no bookends — we can go anywhere we want to with this brand, as long as it's excellent and we love it. But I think that, if I have every single thing that I love to wear in my drawer and I feel like it's all done, if I feel like there's nothing more for me to innovate and that Commando has the industries we should? Then I'm headed to the beach.

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