[tape deck rattles]
- Everything from the late nineties is back.
[both laughing]
- [Narrator] From lower than low-rise jeans
and barely-there bedazzled baby tees,
to bucket hats and coordinated group looks.
- Is that like a blinged out bandana she has on?
I wish I had like a Baby Phat pendant necklace.
- [Narrator] Now, two decades after Bjork turned up
at the Oscars as a swan,
writer Leah Faye Cooper
and VF Fashion Director Nicole Chapoteau
take a look back at the trends and red carpet
that defined and reflected an era unlike any other.
[soft groovy music]
[funky upbeat music]
Who can ever forget Britney Spears and Justin Timberlake
in matching denim ensembles
at the American Music Awards in 2001?
- I think you left out some denims.
It's denim on denim-
- [Both] On denim, on denim, on denim, on denim!
- I've never seen that much denim before,
except for like at a Levi's store.
Britney Spears and Justin Timberlake.
They were this like power music couple.
Everyone was like,
"Ugh, they're going to be together forever."
- Yes. - And like, look at this.
They're so perfect for each other.
They had this little like perfect package,
and then they show up in a matching look?
Like, come on, the insanity of this!
- I know.
I would have loved to be a fly on the wall when,
I mean, I imagine their teams came together
and are like, "What are they going to wear?"
- I know! [Nicole laughing]
- [Narrator] No Y2K it couple encapsulated
the twinning trend more than Posh and David.
- David and Victoria Beckham matched quite often as well.
- All the time.
Like an leather look.
They always match.
And like whatever, they're still together,
destroying the fashion world. - Yes.
- Even J-Lo and Diddy wore matching-ish looks.
It was very much part of like-
- In the same family. - Yeah.
- They had a lot of Sean John moments together.
- 100%.
It was like a part of the whole vibe
is like you guys were like a music group.
- [Narrator] Today, matching looks are born more
out of a genuine love for fashion than for the photo op.
- With the Beckhams, and with ASAP and Rihanna,
these are couples who both parties
genuinely really love fashion.
- Love fashion. - Like they really love it.
- Rihanna will have on, I don't know,
say it's like a Vuitton look,
and Rocky's like, "Oh my God, I love that.
"I want one too, and I want to wear it too."
'Cause he pushes the boundaries with things
that were traditionally considered like,
these are women's looks and you can't wear that.
Where he's like, wear what I want, and I like it.
[funky Latin music]
- [Narrator] On the night of the 42nd Annual Grammy Awards,
Jennifer Lopez showed up in a plunging green Versace dress
that had everyone rushing to their computer
and waiting for their dial-up to connect.
[modem squawking] - [Computer] Welcome!
- Well, it's quite revealing in the front.
Not only the front was so plunging,
but the back, too, was like as low as it could possibly be
without exposing her entire-
- You're almost gonna get a butt crack.
You're almost gonna get it but you're not.
- [Narrator] The dress was so highly searched
on then-fledgling Google,
that the company decided to create
their now popular image search function.
- This is the dress that invented Google image search.
You know, these things then were not readily available.
Like you couldn't just type in what did JLo wear,
and see a picture.
So they really had to build out that algorithm
and be able to do that.
And now we use it for everything.
[funky rhythmic music]
- [Narrator] It was a simpler time.
Before the dominance of professional stylists
on the red carpet,
when celebrities worked on their own
and originality reigned,
look no further than Bjork's infamous swan dress.
A look that walked so Gaga's outlandish red carpet looks
could later run.
- When I first saw it, I was like, "What?"
[Leah and Nicole laughing]
Is she wearing a bird?
- Yeah. - And why?
- It's like ingrained in my mind.
I know everything about the whole look.
The shoes, the tight, the bag was like a little egg.
- It was an egg that she laid.
It's performance art, you know?
She had a handbag shaped as an egg,
which she like dropped from underneath
this huge tulle skirt as if she was a swan-
- [Both] Laying an egg.
- If you saw it today on the red carpet for the first time,
it wouldn't be as shocking, you know?
After seeing like lady Gaga arriving in an egg or-
- Covered in meat! - In a meat dress.
- Yeah. - You know?
But at the time it was quite jarring.
- If I were to look at like probably one of the most
recently jarring, like, oh my God,
this is a crazy red carpet statement,
would be Cardi B at a Grammys.
It was like she was like a pearl emerging from a shell.
Like that is, come on!
It was like so amazing, so epic.
Zendaya when she was wearing all that armor to the Met Gala.
These are like really fantastical looks.
And you're just like, I appreciate them.
I'm like, they took a risk,
they did something that worked for them.
They're expressing themselves, so yeah,
I mean the swan dress is maybe one of the original-
- Yeah, it's up there. - Yeah.
[rhythmic music]
- [Narrator] Lil' Kim made one of the most
infamous red carpet appearances of all time
in a boob-bearing Misa Hylton designed number
at the 1999 MTV Video Music Awards.
- Lil' Kim was just like a style icon.
She took risk.
She did it all.
Like you were constantly like,
"What is Lil' Kim gonna be wearing?
"What is Lil' Kim gonna be wearing?"
Even during that awards show, you know,
the queen mother of us all, Diana Ross,
did a little like boop-boop.
She's was like, "Wow!"
You know, she was a Supreme.
She was like, we would never have shown
that much skin in my time.
- Never! - This is amazing!
And I feel like she actually was like, "I love this!"
- [Narrator] Lil' Kim's lil' pasty
left a big impact beyond the fashion statement
as seen in modern movements, such as Free the Nipple.
- Free the Nipple is, you know,
on Instagram you cannot show a woman's breast
unless it's a piece of art.
And if you show a woman's nipple,
then it gets removed by violating community standards
on Instagram.
So there has been a lot of push
of women, of men, of non-binary people being like,
these are our bodies.
Why do we have to cover them up?
[chimes ringing]
- [Narrator] When it came to Destiny's Child,
Tina Knowles-Lawson wasn't going to let
high-fashion snobbery keep the girls on the sidelines.
- I know that she was like heavily influenced
by a lot of the girl groups that she grew up with.
Like The Supremes,
and how they would wear matching outfits,
or outfits that were matching, but slightly different.
So she really modernized that and ran with it.
- Even the boy bands
or the boy groups from that time period,
they wore matching looks.
There was always like this cohesive aesthetic.
- [Narrator] Destiny's Child's outfits showed
how black artists became style icons
in spite of the industry gatekeepers.
- Do you know if you look at a lot of
the ad campaigns at the time,
everyone is very thin.
Everyone is white.
Everyone appears wealthy.
- Tina was like really influential in being like,
"Okay, so-and-so brand doesn't want to lend to my,"
I feel like they're all her daughters, then fine.
I'll create these.
Let's create a look for them.
[upbeat guitar music]
- [Narrator] It was a time when less was more.
Of exposed thongs, bare midriffs,
barely-there jeans and tops
that threatened wardrobe malfunctions
like the handkerchief worn by Jennifer Aniston
at the 1999 SAG Awards.
- I mean, to wear a handkerchief top on a red carpet,
that's a bold move.
- That's a bold, crazy statement!
I don't think anyone would dare to like
say anything to Jennifer Aniston.
Like, "Why are you wearing that?"
She's like, "I do what I want."
"I'm rich, like, just rich.
- [Narrator] The bandana trend has found a second life
after being spotted on a new crop
of influential taste makers.
- People like Bella Hadid wearing it now.
She's very influential.
So if she wears it, someone else is like, "I can do that!
"I have like a box full of those bandanas and scarves."
So why not?
- I mean, I saw someone wearing one at dinner a week ago.
- From '99 to 2000, everyone was like,
"The world's gonna end!"
Like, "It's Y2K, we're all gonna die!"
And like, I feel like maybe '99 was a time where like,
we were just like, "Eff it!"
Do what you want, wear what you want.
Like be as kooky as you want,
because as soon as it hits midnight somewhere,
we're all gonna implode.
Let's just have fun with it.
[Leah and Nicole laughing]