- I'ma just call all of us out.
The reason we have clutches is
because yes, they're nice accessories,
but it's easier to pose when you're holding something.
Look! Look at this thing I'm holding.
It's easier, but I can guarantee you no one has anything
in those clutches.
You cannot fit anything in them.
Nothing.
[upbeat music]
Hey, Glamour.
Lilly Singh here, and today I'm gonna be breaking
down some of my most memorable looks.
[upbeat music]
Oh! Looking at this picture again, it excites me,
but I also feel like 10 pounds of anxiety.
I won't lie.
The 2019 Met Gala was a movie.
It was a scene.
It was an experience.
It took me, like, 10 hours to get ready for the Met Gala.
The look consisted of this.
This is a Jeremy Scott gown.
The reason I loved it was because it was a flower.
So it's made of petals.
And I thought, "My name is Lilly. This makes perfect sense."
The theme was also camp.
And so it was very over-the-top.
It was very difficult to walk in and to put on.
In fact, it took about four people to lift the dress
over me, and I had to stand still,
and then they essentially installed it on me legitimately,
with just thread and safety pins,
so I could not get out of-
Peeing was not an option.
I could drink no water, I vividly remember.
I had to take a bus to the Met Gala
because the dress was so big.
And my hair, you know, as long as my hair is,
we actually, I think, tripled the length of it
and put in these fresh flowers,
which was one of my favorite hair moments ever.
Then we had this very cool look with the gloves
and the jewelry over the gloves.
Now, here's thing that I didn't think
about is that the rings were so tight on the gloves,
so I couldn't take the gloves off.
And to use any type of touchscreen device,
I had to take the gloves off.
And so I was basically,
throughout the entire Met Gala,
being like, "Excuse me, can you touch my phone
and then point it to my face?"
I couldn't use my phone. I couldn't pee.
I couldn't do anything.
But I won't lie, I do have regrets about this
because I wish I could move.
The necklace and the jewels and all of that stuff,
I'm just gonna keep it real with y'all,
my stylist was like,
"If you lose these, you will disappear.
You and your family will disappear
because these are worth so much money."
And so all of the jewels I were wearing,
I was so tense about losing them.
My head was hurting a little bit
from the weight of this fake hair.
The dress was large,
but the saving grace was
because the dress was so big and long,
you couldn't see my shoes.
And my shoes underneath? Sneakers, baby.
I might have been the only person
at the Met Gala rocking sneakers.
So at least my feet didn't hurt.
But everything else, totally in pain.
[upbeat music]
Oscar outfit.
This is a custom piece by Adeam and I am obsessed with it.
It's one of my favorite looks.
This was a combination of pants
with a belt that had a cape attached with a long jacket.
So it's not actually a skirt or a dress.
I know it looks that way, but it's three separate pieces.
And the reason I did that was
because when I actually got into the party,
I could switch the look by taking off the belt
and it would then be a pantsuit.
The purse that matches fit absolutely nothing.
It was useless, although beautiful, which is much the case
with any clutch I have ever held on any red carpet.
Have you seen an iPhone these days?
An iPhone is six times the size of that purse.
Let's just be real.
My favorite part of this look is definitely the pearls
in my hair.
This was the genius of my stylist,
where we glued pearls into my hairline
and they actually, every single pearl,
stayed the entire night.
Not a single pearl fell, which is pretty incredible.
From the jewelry to the outfit, to the accessories,
I love this look.
Having said that, if you look at the Vanity Fair picture
when my hair is over my left shoulder,
that is happening for a very specific reason.
It's because after the Oscar's finished
and everyone was waiting for their car,
I was being asked by, I believe it was America Ferrera,
who said to me, she was going to the Jay-Z after-party.
And obviously I got no invite to no Jay-Z after-party.
So there I was trying to front being like,
"Oh, no. I think there's another party."
So I was trying to front,
and while fronting and trying to act casual,
I put my arm up on this table,
and I'm like, "Yeah, I think I'm going to like another-"
And she looks at me and she goes, "Your elbow's in coffee."
And I'm like [gasps].
And there was a huge puddle of coffee on the table.
And whatever that elbow, I guess it was my left one,
there's a huge stain on this pure white outfit
that I realized when I got to this party.
And so I went, "Vroop!"
And took the picture, and you don't see it at all.
But that stain is still very much there.
And it is not nice.
No Tide pod has gotten that out yet.
But I still have this outfit.
It takes up a lot of space in my closet,
and I have no regrets.
I love it so much.
This is from my recent TED Talk.
I'm wearing a suit by HEBE.
I hope I'm pronouncing that right.
I am confident I am.
This moment was so nerve-wracking for me.
TED Talks are completely memorized.
It was a 19-minute talk.
I had to perform. I had to say stats with specific numbers.
I had to flip sides, and I had to work with props.
So there was a lot of things going on.
And I remember telling my stylist,
"I wanna wear something that makes me feel so confident
and so secure, but also something that's just me.
I wanna go on that stage,
I wanna bring myself to that stage, and I wanna have fun."
And so this suit just fit so well.
It made me feel so confident.
I, of course, was wearing sneakers.
And I just feel like the reason I delivered
such a great speech was yes,
I rehearsed and I was prepared,
but I just felt great about myself.
The color was striking.
It also completely perfectly matched the background,
which was not a mistake.
I got the stage layout, sent it to my stylist,
and I said, "The stage has to complement me completely."
So it worked out really, really great.
And I'm really proud of this moment,
as nerve-wracking as it was.
Is there perhaps a little bit
of vomit on this suit from being nervous?
Maybe. [laughs]
Now, I've been fortunate enough to sit
at a few seats at a few different tables.
And what I've learned is when you get the seat,
trying to fix the seat won't fix the problem.
Why?
Because the table was never built for us in the first place.
The solution, build better tables.
[audience applauds]
My TED Talk was titled,
"Gender Equity is not Giving Women a Seat at the Table."
And it was all about how throughout my life,
I've had the privilege to sit at many seats
at many different tables,
and they've all kind of sucked
because you get a seat at the table
and your chair's a little wobbly.
And no one else at the table can relate to you,
and you don't get the same resources as everyone else
at the table.
And so I had suggested that instead
of fighting for seats at these old tables,
instead, we should build new, better tables
that actually serve the people that deserve to sit there.
Women.
[upbeat music]
All of these suits are kind of just me, you know?
I wanted to be able to move,
I wanted to be able to be goofy,
and I wanted to be able to...
Again, it's really in my opinion.
Maybe other people disagree with me.
For me, it's really tough to do anything comedic
if you feel restricted.
If I was worried about,
"Oh my God. This is showing. I need to pull this up,"
I would just not be able to perform.
And so all of these decisions are just made
so I can be my authentic, goofy self.
I look at some of them now, and I won't lie,
some of them I really, really like,
and some of them I'm like,
"[smacks mouth] A little questionable."
But for the most part, I really liked my vibe for the show.
I think it was really unique
and brought myself to Late Night.
You know, the thing about doing anything as the first,
and there was a lot of firsts associated with the shows,
is there is a little bit of pressure of conforming
to what people expect that first to be.
And so I do recall for the first season of the show,
there was a conversation
about presenting what my wardrobe choices would be
to the powers that be.
They were all fine with those choices,
but I made it very clear from the beginning
that I don't want-
Just because I'm the only female right now,
I don't wanna do what is expected of a female.
Again, I'm all about de-gendering fashion,
so I didn't wanna do the dresses and the heels.
Sometimes it was suggested that perhaps I do that,
but I never really cared about being feminine enough
or not feminine enough.
I just wanted to be myself.
And so I think, perhaps, I wasn't able to do that
throughout the entire experience and always,
but I definitely think at least
with the way I dressed was very authentically me.
Every sneaker you see here,
those boots right there, I have in my house.
A classic!
Paramjeet and Manjeet Singh.
I mean, are there any looks that are as iconic
as this in my repertoire?
Probably not.
A lot of people don't know this,
but I never had an intention to set out
to dress up like my parents and make them characters.
Prior to this video,
anytime I had my parents in a video,
my friends would play my parents.
I would call my friends over and I would say,
"Dress up like my mom. Dress up like my dad.
And let's just do the sketch."
But I started to make videos so consistently
that my friends were like, "Stop calling me.
I can't come over every day to dress up
for your YouTube videos."
So one day I was just like, "I'll do it myself."
Lilly, you're almost old enough.
We think it is time for us to have the talk.
Mom, I'm 32 years old, okay?
I have a chiropractor.
It's a real outfit, I think, from back in the day,
my mom owned.
I put on these glasses that were a pair of broken glasses
that she had.
And this started what would be a long,
long series of my channel, where I dress up like my parents.
But it was never my intention.
I didn't think people would fall
as in love with them as they did.
The look here is simple.
It's an old Indian salwar kameez that my mom was wearing.
This is kind of gross, but it is so delicate,
the embroidery on it is so delicate,
that I rarely wash it,
and I've been wearing it for literally 10 years.
The dad character, Manjeet.
This is, yes, I'm sad to say,
one of my dad's real shirts.
I know it's a real shirt of my dad's.
I have no excuse for not washing this one.
It's just a cotton shirt, but I don't do it.
It's just too precious to me.
But there was so much black eyeshadow on the collar
from the chest hair that I draw on my chest
that I often forget to take off.
It's happened a lot where I don't take off the chest hair,
and then I throw on a sports bra and go outside,
and someone points out to me
that I have chest chair on my chest.
The wig I also only have one of. It's a scene.
The wig is falling apart.
Also, it's way too big for my head.
It is hanging on by a thread,
but these are things that they're one-of-a-kind.
I don't have duplicates. So I just have to hang on to them.
The beard is also black eyeshadow.
I use a lot of black eyeshadow.
It takes a lot to get it on and off.
But the reason I like playing these characters
is I think they tap into the extremes of my culture.
This is not actually how my parents are.
They make me say that.
This is not actually how my parents are.
Of course, there's traits of my parents that are in them,
but I think this is just me taking certain characteristics
I see in all types of people and heightening them.
But really what I hope people see is a little bit
of themselves in these characters
and a little bit of their upbringing.
'Cause I definitely see that,
and I think a lot of South Asians see themselves
in these characters.
So they're really special to me.
Oh my goodness.
Just a young girl in her youth, here.
"Types of" videos.
When I started YouTube in 2010,
very quickly I found my love for these "Types of" videos
because this was my way of kind
of understanding the world, you know?
Myself being a South Asian girl who went
against all the types I was supposed to be,
with being loud and wearing baggy clothes
and being so outspoken,
I was really intrigued
in just these boxes people get put in.
And so I made videos that would make fun
of these boxes by jokingly labeling people.
Like five types of friends that are annoying.
Five types of parents you might have.
Five types of people at the movies.
And this became a really big hit with my audience.
But something I would do in my videos is I would always say,
"What up, t-shirt reference?"
What up, everyone? It's your girl, Superwoman.
Oh, snap, crackle, pop!
So I would reference whatever was
on my t-shirt to make a joke.
Now, I did this once, and I was like, "Cool."
My audience loved it.
And from that moment on, anytime I went shopping,
I literally would just stare
at the t-shirts and try to think of jokes,
and that's how I would shop.
I would only buy clothes to make jokes
about what was on the front.
So this resulted in, like, hundreds of t-shirts
that were just kind of ridiculous
that I only wore a few times
that are still, 'til this day, in my childhood bedroom.
These shirts literally are still in my childhood bedroom.
It's hard for me to part ways with them.
They remind me of this time right here
in my childhood bedroom
in front of this wall where I kind of figured it all out.
This career that I have stemmed from this.
So they're a little close to my heart.
I vividly remember this top, this pink shirt.
This was an Airbnb I would continuously rent
in LA before I moved here.
And I literally came once a month
and I would shoot videos in LA.
And that reminds me of just this time when
I was so scared to take a step in my career,
but I would keep coming here and keep trying new things.
And so that means a lot to me.
That shirt is associated
with just this fearless energy I have, so.
I'm just gonna have to make a quilt out of it
and just wrap myself in it until the end of time, I guess.
Thanks, Glamour!
It was so much fun to go down memory lane with you.