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Home » I Worked With Anna Wintour. She Was Actually Soft on the Inside.
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I Worked With Anna Wintour. She Was Actually Soft on the Inside.

arthursheikin@gmail.comBy arthursheikin@gmail.comJune 27, 2025No Comments4 Mins Read
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This as-told-to essay is based on a transcribed conversation with Laurie Schechter, 66, from New York, about working alongside Anna Wintour, who recently announced she would step down as Vogue’s editor in chief to be global editorial director. The following has been edited for length and clarity.

I first worked with Anna Wintour at New York Magazine, where I was an editorial assistant in the early 80s.

When she became Vogue’s creative director in 1983, I wanted to go with her to be a fly on the wall of her process. Though she wasn’t warm and fuzzy, she was an incredible teacher.

I continued to work with Anna at Vogue for two separate stints, and at House & Garden, another Condé Nast title at the time.

Working with Anna, I got to know how soft she is on the inside. She’s done amazing things for people in the industry, including me.

I followed in Anna Wintour’s footsteps for a chunk of my career

Anna was friends with my friend before I worked with her.

My friend said Anna was looking for a new assistant at New York Magazine, and I should apply. But I didn’t get the job. A few months later, that assistant quit, so Anna called my office and asked if I was interested. I said yes.

Anna is super organized and is clear about what she likes and doesn’t like. She has a big-picture mind but also drills down to what’s critical and important.

When she moved to Vogue, I asked if she could take me with her, and she made it happen. I took on a coordinator role, where I organized shoots and did picture research.

In 1985, Anna was made editor in chief of British Vogue, but instead of going with her, I went to work for Rolling Stone.

In 1987, Anna took over Condé Nast’s House & Garden. I thought about joining her, but I didn’t know what I would do there. It was Anna who had the idea for me to become a style editor. One of the great things about her is she can imagine something for you and identify other people’s talents. I got to translate my passion for fashion to the world of interiors.

When Anna became American Vogue’s editor in chief in 1988, she invited me to come with her as a style editor, along with others at House & Garden.

A photo of a woman in a dress

Laurie Schechter, pictured in 2023.

Patrick McMullan/PMC via Getty Images



One of the first things she did at Vogue was talk to all the staff. She gave people an opportunity to see what she was all about. Some people decided not to stay on, but others did.

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Anna may be prickly on the outside, but she’s soft on the inside

Anna was very cut-and-dried. Once, I tried to do a page on a theme that wasn’t Anna’s cup of tea. She gave me permission to go ahead, so I did a shoot and brought it back to her. When we laid out the story, she hated it.

I argued my case, and she listened, but she eventually said to me, “Laurie, drop it.” That’s very much Anna. She gave me the chance to change her mind, but if something didn’t work for her, that was it.

People called her “ice queen” or “nuclear Wintour,” but I actually think she has a maternal side she doesn’t show to everyone. A prickly pear is spiky on the outside, but soft and sweet on the inside — that’s like Anna.

I’ve seen her do a lot of things for others, and she’s done nice things for me, too. When I worked at House & Garden, I eloped for my wedding. When I told her, she decided to throw me a private dinner at her house.

I don’t think Anna’s going anywhere

It’s smart for Anna to get out of the day-to-day grind of being editor in chief of Vogue and still maintain a bird’s-eye view on things as a global editorial director. She’s a really good delegator, and I’m sure she’ll make a great selection to be her successor.

I don’t think she’s going to disappear. She’ll probably be in the front row of fashion shows up until she physically can’t anymore.

Anna is a powerhouse and moneymaker. She’s made the industry better in so many ways, and she should be celebrated.

Do you have a story to share about working with a prominent leader in your industry? Contact this reporter at ccheong@businessinsider.com.



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