InStyle Editor: Fashion Is About the ‘Underthink It’ Philosophy

So, I was in a bar with Arianna Huffington the other night. She was talking to me about a Thrive pledge to repeat outfits called #repeats. And hey man, I’m all for it. We’re modern ladies, repeat away! But my thought was this: Can’t it all be easier than that? Can’t we just wear things that make us feel great, be it once or 1,000 times?

This all occurred to me because I am an…under thinker. Overthinking, to me, is fatal. It is an express pass to self-doubt. Have you ever heard anyone say, “I overthought it, and it came out great!” You haven’t, because it doesn’t.

I have a little anecdote about under thinking. When I worked at Harper’s BAZAAR, I chased Hillary Clinton — for about three years — for an interview. In 2011, I finally got it.

Now, this was a whole Situation: I was to tour the State Department and meet six of Clinton’s colleagues. A few weeks earlier, I had traveled with the Secretary and the press corps on a day trip to Quebec.

When it came to the night before the interview and shoot, however, I’d barely written any questions. It was all floating around in my head. Of course, I completely freaked out. I woke up at 4 a.m., typed up something more formal and severely panicked a half-asleep hotel concierge, who I asked to print them out.

By 10 a.m., I was at the State Department for the interview, half an hour in Clinton’s office anteroom. Then something weird happened — I was great. Now Hillary in person is warm and funny, with an explosive cackling laugh, so that helped. But for 45 minutes, we traveled from Wikileaks (one of the first times she’d discussed it) to the power of the pink handbag. “I mean, how can you be unhappy if you pick up a big pink bag?” Hillary said.

When I listen to the recording now, I’m still shocked. I sound like I know what I’m talking about, like the editor I am on paper. It was bizarre — and one of the most gratifying experiences I’ve ever had. Now sure, I hadn’t prepped like an eight-year-old in a spelling bee (and that 4 a.m. stunt wasn’t particularly wise). But everyday, I’d paid attention, from politics to that Ferragamo pink bag. And that attention paid off.

Even then I had, of course, asked Clinton what she’d be doing in 2016. “Beaches,” she replied, “Beaches and speeches.” (But I think, given 2016, girl deserves a big pink bag).

My Underthinking mantra was only verbalized a couple of years ago, because guess what? I underthought it. Thankfully, I’m not the only one who feels this way. I once did a talk with J Crew’s Jenna Lyons, who is a thoroughly wise, no BS girl’s girl. She was asked a question about “getting ahead” at work. Her response to this was:

Think about what you want to do and what you love. You’ll never be successful if you spend too much time thinking about how you’re going to get ahead. Get ahead by doing something that you love and committing yourself to that. Then you’ll be happy, you’ll work hard, and you’ll get noticed.”

And that’s it, isn’t it? We ladies know what we’re doing, we just have to trust it more. And underthink it.