Anna Wintour Quotes

I was perhaps the worst student you have ever seen. You know, I thought I was stupid, all my classmates thought I was stupid, so there was general agreement.

I was always behind in class. There was people in my class who was amazing at art, amazing at maths, amazing at English, but I wasn't clever with anything, even though I tried my hardest.

I've always been a mediocre student, so I never won an award in school. I'm not very athletic, so I've never won a sports award. So, I'm a mediocre person.

I longed to be bright and most certainly never was. I was rather hopeless, I suspect.

I had a pretty bad time when I was an undergraduate at Cornell University. I failed out of school. I was much, much heavier.

I had this inferiority complex as a child, as I was not good at speaking. I was also not good in studies or sports and would often flunk in four-five subjects.

I was 23 years old, a freshman at university, and there I was, on the first day, sitting in a remedial English class. I was so ashamed I almost got up and left, but somehow I knew inside that if I ran away from this, I would hate myself forever.

I'm full of self-doubt. I doubt everything I do. Everything I do is a failure.

There is a very good chance I could have been a screw-up for the rest of my life.

I failed first grade, which is my biggest problem. You always feel like a failure, like you're stupid.

I started out in the journalism program, but I got kicked out. I wasn't very good at it. It wasn't where I wanted to be ultimately.

What fascinated me most was Churchill as a young child. He had a kind of Dickensian childhood. The neglect. And he was a terrible student. His whole life is a study in trying to overcome your feelings of inadequacy.

I'm a dreamer, and I'm a perfectionist, and I love excellence, and that's hardwired in me. But when I was young, I lived in a space for a long time where I only felt insufficient.

You try to be the best you can and sometimes it ain't damn good enough.

I'm just propelled by insecurity; that's what really leads me to want to do better.

I understand that feeling of insecurity, like you're not good enough as you are, and you need to change.

I didn't finish college, and I was very sad about that because I don't think I gave myself a chance to learn, to prove to myself that I could learn.

One of the things that has inspired me so much is knowing that I felt like I could never measure up.

It is always our inabilities that vex us.

Someday, we’ll run into each other again, I know it. Maybe I’ll be older and smarter and just plain better. If that happens, that’s when I’ll deserve you. But now, at this moment, you can’t hook your boat to mine, because I’m liable to sink us both.

In terms of work, I never felt that I've done it right. I always want to have done it differently, to have done it better, a different way.

I never felt good enough about myself. I could be better at this, I could be better at that. I could look better. My work could be better. That whole idea that you're going to get caught, you're going to be found out as a fraud. That's one of those reasons I got up at 2:30 in the morning.

A lot can change because you are embarrassed by something.

We can't be as good as we'd want to, so the question then becomes, how do we cope with our own badness?

I had no confidence at school. I was not a good student and I really thought I was pretty stupid. Just dumb.