- I absolutely love being a stylist.

These, Selena wore them and it sold out.

The clothes that you wear tells people who you are.

And with each one of my clients, what I am thinking about

is their body and their style, and their style is both

their taste and my version of them combined.

I think I always was drawn to fashion,

I can't really pinpoint a time when I wasn't.

My first word was shoe.

(laughs)

A lot of my memories of childhood are tied

to what I was wearing.

My great-grandmother collected a lot of carpets

and antiques and crystal, and it was important to my mom

that I know that these things were precious

and that they were special.

There is this real appreciation for beauty and art

and adornment, and I was taught to value that,

that that was a pleasure of life.

I just took it to an extreme.

I grew up in Easton, Pennsylvania.

We came to New York all the time.

I always dressed myself and always chose what I wore

and I really loved saddle shoes and I had little shoe polish

'cause I liked to make the white super white

and I'd polish them every day.

When I was super little, I was allowed to read magazines

at the libraries.

I wasn't allowed to read Cosmo 'cause it's racy

but I was allowed to read Vogue and I loved YM,

Sassy was amazing, I loved Interview when I was little.

I think my family was always supportive

of my love of fashion, but I don't think anybody

considered that working in fashion could be a career.

I remember when I was like 16, a friend's older sister

was going to FIT and I came home and I said to my mom,

do you know there are colleges for fashion?

And she like laughed.

And that was sort of the end of the discussion.

So then I went to college and I studied English

and Art History.

At that point, I was like, I want to work for a magazine,

I knew I wanted to work for a magazine.

That was super important to me, it was sort of in my mind.

I tried to live in LA for a little while but I'm from here.

My friends are here, my family is here,

and I don't know how to do fashion anywhere else.

I got an internship running the closet

at Lynne Franks and I got to work at London fashion week.

It was like eye-opening, it felt great.

I lived in this cool apartment and we went out all the time

and I felt like I had a really good job.

I didn't want to come back.

My parents weren't psyched, I don't think

they were impressed by the whole situation.

Yeah.

(jazzy music)

I came home for Christmas holiday

and Kati Korbiyako was the art director at Glamour Magazine

and she had two boys who were my friends.

And I called Kati and she said, oh Kate Young,

I've been waiting for you to call me

since you were 12 years old.

Let's go to Human Resources.

Sarah Slaven was there, she was like the Human Resources

god at Conde Nast.

She took me to Paul Wilmot and Paul took me

to Anna's office.

This all happened like.

- Yes!

Oh my god, I was totally nervous, I was 20 years old.

Flew back to England, quit my job, moved out of my place,

started working as Paul Wilmot's assistant

and Paul Wilmot quit like the second day I worked there.

But I had just met Anna and Anna's assistant quit that day

so I went back down to Anna's office,

interviewed with her, and got a job in her office,

so it all kind of snowballed very quickly.

- Anna Wintour's office. - You know, I insist

on interviewing all the assistants because we're going to

invest two or three years of time and training

into these young women, they have to be promotable women.

- I can tell you what I was wearing.

I remember I was wearing Tom Ford Gucci velvet

drainpipe trousers and Patrick Cox boots

and like a silk shirt, probably just like what I have on now

and then she knew Lynne Franks so she looked at my resume

and was like.

But she said something to me in the interview,

she was like, you know, this is a tedious job,

this is a difficult job, working for me,

but if you're good at it, it'll be worth your while.

- [Man] Anna Wintour!

- I had a really hard time watching Devil Wears Prada

because my perception of the experience was so different.

I never felt like I was being taken advantage of

or that I was disrespected in any way.

I was like, I'm getting Anna Wintour coffee.

I was so excited that she gave me a couture dress to clean

and I could, I had never held a couture dress before,

I could open it up and look at it and see the beading.

So Vogue was actually the first place where I felt seen,

I felt like, oh, I can talk about shoes for 15 minutes

and you won't think I'm dumb.

I'm going to talk about shoes with two girls

with Ivy League educations for the next 35 minutes

and we're going to be really serious about it

and it was the first time in my life that I could do that

and feel validated.

(somber music)

I wake up incredibly early and it's often still dark out

and no one else is awake.

Things are still and quiet and I can think

and drink coffee.

I just love it.

I have ideas all the time and I'm constantly like,

oh, I should do this, I should do this.

- Hello! - Hi!

- Good to see you.

- I like this one.

I really enjoy making things and finding an outlet

for creative inspiration, but the thing that's really

exciting about optical is it's not a season like fashion

that just disappears, we just keep selling them.

So the collection is getting broader,

we're not really losing any of the old styles.

Which is really satisfying as a creative person,

it's really nice to not have your work just like go away.

You know?

- No is not an answer.

So if she asks you something and it's impossible,

come up with seven other ways that you're going to accomplish

something very very very similar and present them to her.

Done.

It's a great way to know how to work with celebrities.

No is a cop-out, there's always an alternative.

I think the first celebrity that I styled outside

of magazines was Jennifer Connelly and we really got along

and so that continued from there.

I think this is the dress that Margot wore to the Oscars

in 2016, and this is the sketch from Tom Ford.

There have been times when I've done an awards season

with clients where we have a mood board

and we have a plan we're sticking to.

And then there are other clients who I just kind of know

how I want them to look, but I mean, it has to suit them,

they have to feel comfortable in it,

it's not like some thing I create and push on them.

I met Selena because she was ready to change

and she was so open to sort of anything, it was exciting.

- Selena, you're up! - And it was like

Salron, Dior, and Valentino.

Like, let's raise the bar.

This is the dress Selena wore to the Victoria's Secret show

a few years ago.

I had this idea in my mind that I wanted her to wear

a dress that was like a swimsuit

and that's for the mic pack.

Do you appreciate that?

This is Dakota's dress from the Met,

it came with all the embroidery.

I think it's easy to talk to movie stars about movies,

it's what they, that's what they know, it's their business

and it's also to talk about characters through the lens

of cinema, and I think it's important to have

some sort of voice, some sort of identity.

It's these tiny little gestures and details.

Each person or story or designer needs to have

this very clear vision that is maintained throughout

so that it's recognizable and that there's a strong

narrative thread for each client.

I think that whether you like it or not,

your clothes say a lot about you to other people.

(classical music)

- Selena! - Celebrities,

when they're doing press and red carpet,

they're trying to communicate an image

that will help to promote a film, and also promote

themselves as business people, as actors,

so I want to create an image that's as true to their idea

of themselves as possible.

I do this 'cause I really am connected to a magical dress

on a real woman who is the woman everybody cares about

for something she created that touched people this season.

The woman of the moment in the most amazing dress

walking is exciting to me, on a really fundamental level.

Everything's so different from when I first started,

magazines were king and people bought fashion,

I don't know what's happening anymore.

I'm doing the same thing I've been doing for 20 years

but people care about it now.