If anyone knows about making a successful career and life pivot, it’s Michelle Smith.
In 2019, the designer ― who has dressed Michelle Obama, Jennifer Lopez, Mika Brzezinski and more ― left Milly, the fashion empire she built with Andrew Orshin, who she married in 2003 and separated from in 2017.
It was a low point for Smith, 48, especially after experiencing incredible career highs. During the company’s peak, for example, Milly was raking in $50 million in annual wholesale revenue. And in 2018, Smith was tapped to design Obama’s dress for her official portrait that hangs in the Smithsonian’s National Gallery in Washington, D.C.
After selling Milly to apparel company S. Rothschild at auction for $5.7 million, Smith described feeling burned out, but ready for a new start. She took some time to reset, and in October, the mother of two launched a new, namesake brand (amid a global pandemic). She traded the Milly signature look of vivid colors and prints for a style she described as minimalist and time-honored.
“My style has evolved, and so has the way I dress and the way I want women to feel and be perceived … I’m feeling less is more. Maybe it’s the confidence that we develop as we get older through our life experiences,” she told Brzezinski in a recent interview.
One of the last pieces Smith designed under Milly was Brzezinski’s wedding dress, a tea-length garment with swiss dot lace sleeves and an overlay that reached past the hem of the skirt.
Smith chatted with Brzezinski about the genesis of that wedding dress, making a clean break from Milly, creating a new career path for herself, her best advice for young women and more.
Below is their interview, which has been edited for brevity and clarity:
Mika Brzezinski: Michelle, first of all, the woman behind my wedding dress. Can we talk about it for one second? It was one of the last projects you did with Milly and it got an incredible reaction. I know it wasn’t about me, because I never get that reaction. Explain the reaction that dress got. And what was your thought process when you were making it?
Michelle Smith: It got so many media impressions. It was really incredible. There was something about it that had just such a universal appeal…
You were really easy to work with, because you had a vision of what you wanted. So, I was able to springboard off your initial tear sheets and ideas. At the same time, we found fabric that I thought would be fantastic for your dress. It was that sort of velvet, pin dot fabric tulle, which is gorgeous couture from Europe … I had just been sitting on it, wanting to use it and I didn’t know what to make with it. And then you came to me with, “Hey, would you be interested in making my wedding dress?” And I was just so excited. I knew that I wanted to propose that [fabric] to you. The [dress] shape that we worked on was form fitting and very modern. Just through our fittings and having our chit chats together, the whole process was so enjoyable, an honor and so much fun.
Brzezinski: So much fun. It made the day. And so much has happened since then. As your friend and admirer, I’m proud of you. I told you sitting in the dressing room of your Madison Avenue store when you were talking about making a career pivot, I said, “Oh wow, this is going to be the best thing that ever happened to you.” Did you believe me then? And tell me how things are going now?
Smith: That’s funny, I remember I was sitting on the floor of the drafting room talking about it. I was really scared because so much of my identity was tied up in Milly. I had launched my business when I was 27 years old ― before I was married, before I had children. And I felt very much intertwined with that identity. And I wondered, “what was it going to be like on my own now?” … I was scared. But at the same time, I was also kind of excited for a fresh start because I felt so burned out by the time it was over after 20 years of having that business and having it grow so big. And it really became a big machine. It was impossible to slow it down. It felt good to just step off that crazy carousel and take some time off and regroup and reset and really think about my next steps.
Brzezinski: During Milly, you had achieved such great success. You designed the dress that Michelle Obama wore in her official national portrait. It was 100 percent your creation and an incredible nod to your talent.
Smith: Thank you. That was a magical moment. One of the ultimate achievements I think as a designer, is that right there. [The dress] has a permanent place in American history in a way, and my children will see the portrait, and so will their children, grandchildren and great grandchildren, and they’ll know that it was me. So, it’s really emotional and really special.
Brzezinski: So here you are now. And I consider the work that you’re doing to be next level, but your work at Milly swept up an entire generation, several generations of girls and women. But there’s something different about your new fashion line, and I wonder what it is about your life, what it is about you and how you have evolved that influenced your new venture. Smith: I think there’s a much more minimalist aspect. I’ve definitely evolved as a designer. My [first clothing launch] was at 27 and now I’m 48. My style has evolved and so has the way I dress and the way I want women to feel and be perceived … I’m feeling less is more. Maybe it’s the confidence that we develop as we get older through our life experiences. The pandemic also had something to do with it, because I launched my business during Covid-19. I definitely retooled my collection to very much be relevant for wearing at home or taking Zoom calls, for the way we were living … Eventually as things get back to normal, I’ll incorporate more going out pieces, but they will definitely have this more evolved, signature look of minimalism and clean lines. Brzezinski: You may have heard, but Know Your Value is partnering with Forbes to highlight 50 incredible women over 50. Many of these women are like, “What? Stop working? What are you, crazy?” I don’t know what you thought 50 looked like for you, but I’ll be honest. I didn’t see myself. I never thought about this decade, but I thought about my 30s, I thought about my 40s, but I literally never thought about my 50s. Did I not think they were going to exist professionally? Smith: Oh my God. Same. It’s something we never contemplated. Isn’t that funny? And here we are. I remember when I was a little kid and my grandparents were pretty young, they were in their 50s They seem so old to me. Now, 50 feels so young and fresh and amazing, you know? Brzezinski: Exactly. So where do you want to take your line? Where do you want this to go? Is the sky the limit? Bring me back to rock bottom and where you are now. How are you feeling about things? Smith: As I mentioned before, the Milly business had grown so large, and it became really overwhelming for me. I was designing hundreds of collections a year, thousands of styles … It was too much pressure, too many different clients, wanting different things that weren’t necessarily on brand. It feels really good right now though. I re-launched my Michelle Smith brand in a very small, very controlled way, purely direct to consumer … It’s smaller business, but it also means I have so much more control. [With Milly, there were mistakes I] made … I won’t make those mistakes again. So, building it from the ground up and having a really important part of every single piece of the business and really knowing it intensely and living it, it feels amazing. And for now, I would like to keep it very curated and carefully thought out. And for many reasons it’s more enjoyable that way… I’m also going to do a collaboration with the Smithsonian. The official Obama portraits, they’re going to be traveling to several museums over the next few years. And I’m going to create some exclusive products for the museums inspired by the dress and collaborate with the museums to talk about the dress… And I’m just focusing on growing my brand. [Amid Covid-19], I think as entrepreneurs, we need to stay very nimble and flexible and almost like a cat. Just be able to move quickly and pivot…Luckily, [before Covid-19], I hadn’t taken office space yet and I was going to launch wholesale and then I pivoted and I decided to launch direct to consumer. So, looking at the cues and the signs and being able to be flexible and nimble, I think is really important for any entrepreneur. Have the antenna up and don’t be afraid of change.
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