- [Cassie Anderson] I grew up watching Lindsay Lohan.
She is an icon.
I know that a lot of people
are probably gonna be looking at the pictures,
watching the interviews, and I felt the weight of that.
My name is Cassie Anderson.
I am the Fashion Director at "Cosmopolitan Magazine".
I style all the cover stars,
and this is how I styled Lindsay Lohan.
It's the day before the Lindsay Lohan cover shoot,
and there's still so many things that need to get done.
Before I start styling someone,
I do a deep dive on their past editorial and red carpet,
and Lindsay did a cover in 2006 for us.
She looks good.
I don't think a lot of people know what it's like,
because I do get a lot of questions.
How do I get them to put on the clothes
that I want them to put on?
How do I make sure that they're staying in a good mood?
Those are all parts of my job.
Not just picking out the fashion,
but it's working with the person.
Something that I take very seriously,
is making sure the talent looks and feels their best.
I need to make sure
that all of the clothes tell a story together,
that the clothes makes sense in the location,
and that everybody is on board,
from our editor-in-chief to the talent,
to the photographer, our creative director.
We all need to put our stamp of approval on it
before it hits the lens.
I always have a vision.
There's something behind the story,
so we wanted to take nod to Lindsay's return to the theater.
I always print where we're shooting,
so we're gonna be at the Roxy tomorrow.
I see Lindsay looking beautiful in a Jean Harlow situation,
something from old Hollywood.
We wanna make her look strong.
She's back, she's powerful.
This is gonna be beautiful once it's steamed out.
We have a run through in an hour,
and the run through is when I present my thought process
and the clothing for our editor-in-chief, Jess Giles,
and we scramble to the finish line all the time to choose,
and Jess will weigh in
and says what she likes and what she doesn't like
and sometimes not everybody agrees on their favorite pieces.
I have this Carolina gown here,
which I know is gonna look amazing on Lindsay.
I don't know if it's gonna get approved.
But it's always nerve-wracking to present your work, right?
I have prepared for a few different scenarios.
So a smart stylist always has a backup.
If creative isn't being agreed upon, then, you know,
I should pivot.
So after the run through,
if there are things that I don't have
that people have asked for,
then I'm gonna go on a few store pulls.
Lindsay loves Chanel, so we got her Chanel.
She loves Saint Laurent, so I'm doing a pull later today.
Lindsay's been around for a long time.
She knows what she likes
and she knows what she doesn't like.
Not only was I able to get a list of brands that she loves,
I, of course, studied her red carpet,
and was able to see what looks best on her.
You know, the shoot's tomorrow,
so it's always nerve-wracking
waiting for those last bits of clothes to come in.
(cheery music)
I can talk you through the racks?
I thought that these would be...
- (gasp!) Yes.
- [Man's Voice] Yeah, those are so cute.
- [Cassie Anderson] She's like maybe eating popcorn
or something?
- Yes, it's so I'm-
- [Woman's Voice] I'm obsessed.
- [Woman's Voice] I think so.
- Yeah. It's so gorgeous and it's, it's very much
that sophisticated, smart, it look good against red
or the sea-foam green, like velvet, like curtain background.
We're getting with a matte red lip or something
- [Cassie Anderson] This is vintage Valentino
which reminded me of a film strip.
So I thought it could be really cool tied to the location.
- This is a gorgeous, gorgeous object.
- [Woman's Voice] It's really stunning.
- [Cassie Anderson] Nice. If we were to do one evening...
(women talk over each other)
...Like this
This is what I'm seeing
Not her on the stage or you know,
or you know, putting on a play, but
- [Woman's Voice] Okay.
- [Man's Voice] Yeah. One moment.
- [Woman's Voice] Maybe she's at...
- [Women's Voice] One moment..
- [Woman's Voice] If you bring in the popcorn
or something like that.
- [Woman's Voice] Casuals it up a little bit.
- [Cassie Anderson] So Lindsay requested Chanel,
I have this amazing
- [Woman's Voice] I think that's great.
- [Woman's Voice] Love it.
- [Woman's Voice] Yeah. Yeah. - [Man's Voice] I love that.
- Great. And this, this is Versace Couture
- [Woman's Voice] Oh wow.
Yeah. This would look killer on her.
- [Woman's Voice] Mmmhmm.
- This I've been waiting to ask you about.
- [Woman's Voice] I love that too.
- [Cassie Anderson] Yeah.
So this is the - [Woman's Voice] It's amazing
getting ready scenario. - [Woman's Voice] It's so good
like the boudoir moment, in the dressing room.
- [Woman's Voice] Yes.
- So we're gonna have a dressing room set up.
I'm gonna pull more color this afternoon.
- Okay.
- But this is what's here so far.
- [Woman's Voice] The environment is very red.
Like there's saturated color almost everywhere.
I think that like the whites will look great.
I think even the blacks will pop,
especially the sparkle with her flash.
- [Woman's Voice] For the glam moments.
I love the black and white. I love the Chanel.
- I wonder if this is a little bit
of a sweater shoot. Like cashmere.
I just, her skin, her hair.
And that helps us
with the intimacy that we've been talking about, the smarts.
There's this beautiful reference image that I have pulled.
I'll send it
to you where the model has a turtle neck, cashmere sweater.
It's oversized and she's like pulling it
over her knees and is like a very like intimate moment.
- Yeah! That. And we could also get some of this cute stuff.
- So this is in route.
If it doesn't make it today, it will make it tomorrow.
This is a backup.
- [Woman's Voice] Right. We wouldn't shoot them both
We shoot them if... - Correct.
- [Woman's Voice] Yep. Yep.
- [Cassie Anderson] We have a back up.
- [Woman's Voice] Yeah.
- [Woman's Voice] Yeah. Love that.
With maybe the gloves?
Here's what we still need.
We need sweaters, - [Cassie Anderson] Mmhm.
for the coziness.
- [Cassie Anderson] Yeah.
- We need some additional
suiting - [Cassie Anderson] Mmmhm.
and then we have it.
- [Cassie Anderson] I'm headed to look for Jess's
suggestions for Lindsay
and hopefully I'll find what we need.
Hello.
(Cassie's footsteps)
So we're down in the vault right now, which is the,
"What Goes Around Comes Around" V.I.P. shopping experience.
It's by appointment only
and not a lot of people know about it.
So there's a lot of treasures down here.
Jess told me in the run through that she wanted sweaters.
So sweaters she will get.
I need suiting.
There are some gorgeous pieces on this rack.
Let's pull this.
See, I'm gonna hand you that.
This one has nice color, Versace, little knitwear
and let's do this knit too.
All right, let's move on.
- (salesperson says something in the background)
Yeah, it was great!
All right, so I've been running
around trying to get these last pieces for the shoot.
Got some knits from the run through feedback
some more suiting pieces.
I feel a little bit better after this pull
but it is down to the wire, a little stressed out
that we might not have everything that we need so
we have some more clothes trickling in.
If Jess doesn't like these clothes
I don't know what I'm gonna do.
Then I got this, Anthony Vaccarello.
- [Jess] Lovely. Yeah, that's exactly what I was picturing.
- Do you have that Christian Siriano?
- [Woman's Voice] That was confirmed.
- [Woman's Voice] Ooh!
- [Woman's Voice] This confirmed,
which is also - [Woman] Oh!
Major! - [Woman] That's amazing!
- [Cassie Anderson] Right?
- [Jess] Wow!
These I'm obsessed with.
This is such a cool thing.
- [Cassie Anderson] Those are actually my personal
shoes that I'm
loaning to the shoot.
- No, really?
- [Cassie Anderson] Oh yes. - Wait, they're flawless
- [Cassie Anderson] I've done it before.
- Have you not worn these before?
- [Cassie Anderson] I haven't, nope.
- From the Cassie Anderson archives!
(Cassie laughing)
- This is incredible!
- [Man's Voice] Oh, I love that.
- [Woman's Voice] Wow.
- [Woman's Voice] It's gorgeous.
- [Cassie Anderson] Red carpet ready.
- [Woman's Voice] Naked, underneath?
- [Cassie Anderson] Oh yeah.
- [Woman's Voice] Mmhmm. Mmmhmm.
- This is great Cassie.
- [Woman's Voice] Nice job.
- We pulled it together at the last minute.
- [Cassie Anderson] As we do.
(Cassie and Jess laughing)
- Good.
- [Cassie Anderson] So just finish the fitting.
It went really well.
I think everybody's super happy.
It was one of the smoothest fittings that I've ever
had before.
You know, when you buy something off the rack
it's not gonna fit head to toe perfectly.
There was this little Alexander Votie dress
and we were all a little bit nervous.
She put it on.
We were all blown away.
At the end of the fitting.
We had too many options.
- Lindsay's most excited about this.
- [Cassie Anderson] Then we're gonna move
on to the cover shot, which is the Votie.
The hardest part of my job is the responsibility
of making sure the talent looks and feels their best.
That's something that I take very seriously, so we just
need to make sure
that all of these are steamed, prepped, ready to go.
Time to get dressed!
Lindsay arrived early and was one
of the most professional people that I've ever
had the pleasure of working with.
I think that she was just so nice, so lovely
and as far as I could tell was having a great time on set.
My favorite part of the day with Lindsay was
at the end when she asked me for my phone number and
she texted me, thanking me, and he took a picture together.
My job is awesome, even
though it's a little bit stressful at the end of the day.
It's amazing to see the work come together
into the photos that I know the fans will all love.
If you have any questions
on what it's like being a stylist, drop them below.
(cheery music)