Pictured: Cindi Leive

Over the course of her dynamic career, Cindi Leive has interviewed everyone from Malala Yousafzai to Michelle Obama, and covered a wide range of topics, from lipstick to legislation. We are thrilled that she is lending her years of experience and expertise in the media and fashion worlds to her latest gig as host of The Barneys Podcast. Throughout the season, Leive brings depth and humor to her interviews with dynamic personalities including Thom Browne, Alexander Wang, Phoebe Robinson, Victoria Beckham, and more.

In Breaking the Dress Code, we turn our attention to our host to learn how she’s navigated her brilliant career and what she’s learned along the way.

The Window: How and when did you know you wanted to be a journalist?
Cindi Leive: Well, my childhood idols were Harriet the Spy (the snoopy kid with the notebook) and Brenda Starr (the glamorous journalist comic-strip character), so I guess my path was obvious! When I was eight I created a magazine produced by all the kids on my block, or tried to, anyway—no one was as enthusiastic about it as me. In high school and college I worked on the student newspapers. I was always drawn to the feature or lifestyle sections, where you got to explore people’s lives and emotions, and where the pictures were more likely to be in color.

When you started as EIC of Glamour, what was one of your most important challenges you faced in your role?
On a big-picture level, it was exploding people’s ideas of what a “women’s magazine” could be or do—pushing through old stereotypes that said if you covered fashion you shouldn’t also cover politics or social issues or news. Obviously women can hold two thoughts in their head at once, and so can the brands that serve them. I hope we proved that, at least a bit.

On a personal level, in my first editor-in-chief job—which was at Self, prior to Glamour—I went from managing exactly two people to managing 50. I had to learn to ask for advice about how best to deal with tricky situations and tricky people, and how to get the best from a team. I always tell women now to ask for advice when they’re in their first big job running a team. There’s a myth that if you’re a reasonably nice person and know what you want, it’s going to come naturally. The truth is, it’s like everything else: You have to learn.

Cindi Leive photographed at Freds Beverly Hills wearing Erdem.

You’ve interviewed so many inspiring people. Which ones stick out as career-defining moments?
So many! Skyping with Malala Yousafzai before she won her Nobel Prize was a high point. And the two interviews I did in the White House—with President George Bush in 2007 and First Lady Michelle Obama in 2015—stand out, too. It’s pretty impossible not to walk into the Oval Office, as my colleague Wendy Naugle and I did for the Bush interview, and not feel the weight of everything that has happened in that room before you were there. We were told that Bush always ran early, very early, and that we should arrive two hours ahead of schedule, which we did. Good thing, because he was ready. For the interview with Michelle Obama, the vibe was much more relaxed. I’d met her multiple times before, and was interviewing her alongside Kerry Washington and Sarah Jessica Parker about their initiative on military families. But still: You’re sitting there under portraits of presidents, and you think, I’ve really got to get things right.

What has been one of the most difficult things about your success?
It took me too long to realize that longer hours and crazier schedules don’t necessarily make you better at your job. Ultimately, if you burn the candle at both ends you have no candle. I spent a lot of years running in airports, checking email at 2 a.m.—same as a lot of my peers. It took me until I was about 40 to start realizing that it wasn’t doing anybody any good, and I was setting a crappy example for people around me. I do better now!


You’ve famously encouraged one of my personal favorite mantras, “fake it ’til you make it.” Tell us about a career moment where that worked for you.
Well, to clarify, there are certain things you shouldn’t fake: knowledge, for instance, or hard work. If you care about what you’re doing, you’re going to have to work hard at it, period. What I mean is that it’s okay to fake confidence. I think there’s a misconception that you have to feel completely fearless before you take something like an assignment or a new job on. You know that old expression: Courage isn’t the absence of fear, courage is fear that has said its prayers? That’s really true—if you’re doing something big or new or risky, you’re going to feel terrified. That’s okay. Do it anyway!

You’ve been in media for more than two decades. Tell us about one of the biggest changes you’ve witnessed regarding women and media.
I think women now demand more from media. They expect the media to represent them, to listen to them, not to feed them condescending or biased material. They understand that “the media” is a bunch of individual people making decisions about what gets printed or aired or run, and they want those people to listen to them. This is wonderful and healthy!


What do you think is the biggest change in media as a result of the #MeToo movement?
Well, I hope one change will be that more women will be in charge. I’m a huge believer in journalism, but it pains me that the media industry actually lags behind other industries when it comes to female representation in the top ranks. Only 17 percent of media execs globally are women. Nothing changes ’til we change that!

What’s the relationship between your personal style and your career? How have the two evolved together and influenced each other?
Well, certain things about my style have been pretty constant over the years. I like dresses with waists, color, pattern, denim, and because I’m five-foot-two, heels are almost always in the rotation. I admire a slouchy Annie Hall menswear situation, but it’s not really for me personally! But I’ve definitely gotten looser and more casual lately—partly because of my own life, which is more entrepreneurial, less corporate than it used to be, and also because of what’s happening in fashion. Everyone’s more casual, more active, and for women in particular, ease is really important. Anything that hurts is just out, which is exactly as it should be, right?

We are so excited to have you as host of The Barneys Podcast Season 2! Why did you want to take the gig? What excites you about podcasts?
I’ve become a podcast addict over the last year, like the rest of the world. And this one appeals to me because, honestly, my favorite part of fashion shows is always the conversations you get into in the front row—and, during my early years, the back row! Sometimes the outside world sees “fashion people” as shallow or tyrannical, but some of the most interesting, creative, committed, thoughtful, funny people I know also work in fashion. We want to bring that all alive. And, of course, our guests won’t just be from the worlds of fashion—they’ll be from the worlds of culture, art, and definitely social change.

Beyond The Barneys Podcast, can you tell us what you’re up to?
My book is a memoir, but it’s also about women and progress. I’m loving working on it, and I’m doing speaking engagements around the world as well as a fellowship at USC and two TV projects while I work on it.