- I've been trying to remember when the last time
I wore a dress was, and I can't.
(upbeat music)
I'm sure that I wore one on my eighth birthday.
Always have hated dresses, always.
I imagine that you would feel very liberated wearing a dress
so I wish that I liked them.
I definitely like them on other people,
I just don't feel comfortable, personally, in them.
This is going to truly be a challenge for me.
I'm gonna feel pretty bad, I assume, for most of the day.
When you've looked a particular way for a really long time,
you become afraid of looking anything outside of that.
My ideal dress is just a really long shirt.
(cheeky music)
She looks nice with her beanie.
That's something I would wear.
It just looks like a long T-shirt.
It's pretty short, but can I wear stockings underneath?
- [Narrator] No.
- No?
Alright, that's a maybe.
I don't like this one 'cause it's got
this like open part here, where it reveals the side.
It's loose but you can tell that she's got hips and a butt,
and that's stuff that I don't normally
shout out to the public, so no.
This is a red and black, so there's a bit of color here.
Not too much.
Leopard print shirt-dress.
You really want me to show my legs.
I think this kind of suits my style,
but still, that's so much thigh, man.
No.
Damn, that side split.
It's black.
That would be really challenging, cause that's, like, sexy.
I like this one.
That's mad.
See, this is what I'm talking about.
Actually, I really like this 'cause of all the texture
and that pleat skirt.
And it's just like this boxy-ass,
boring, black, long T-shirt.
I love it.
I left the house today and had to turn around
'cause I realized that I hadn't shaved my legs.
Not that you have to, to wear a dress,
but it was the first time that I actually cared to.
I'm so tired.
I'm getting my period, so that sucks.
When you're about to put a dress on for the first time in,
what, 20 years.
Dress number one is how my insides feel right now.
(groaning)
I feel like I'm not wearing anything at all.
I feel really free and cold, but mostly free.
Overall, it doesn't feel as bad as I thought,
and it's not as short as I thought, too.
I was really afraid of it being short.
I hate it.
I just straight-up hate this one.
I thought I would like this one the most.
It kind of feels like a uniform
for some kind of conservative cult.
Get outta here.
God damn it.
Fucking look at that slit.
Look at my leg, already.
It's just poking out there.
Oh, God, look at that butt.
I don't know what to do with my body.
This one makes me feel the least comfortable
out of the three options.
Maybe it does look good.
Right now I feel terrible.
I don't feel confident at all.
I wish I wore better underwear.
See, these are things that people who wear dresses
have to think about.
This is like combating so many fears at once.
Maybe, it might increase them.
Time will tell.
(upbeat music)
(cooing)
Let's see how many stairs I can do now.
This is kind of fun.
- Wow, yes.
Yes, approved.
Elegant, it's very elegant 'cause it's sleek,
it's black, it's really cute.
So it suits you.
- It's more aligned with your style
than I would think it would.
- Yeah.
- Yeah, somehow it works, I don't know.
- So, I saw you from far away, and I was like,
"Oh, that looks like Tan, but she's wearing a dress,
"that can't be Tan"
I think you look good.
It's a little bit strange that I've never
seen you wear a dress before.
- I haven't.
- It's a minor thing, but.
- I haven't actually warn one for 20 years.
- 20 years?
- Yeah.
- It is interesting how you define your personality
by what you wear.
When you change it, you realize it's all a performance.
- I'm locked out, hanging out in a stairwell.
Normally, the security pass is attached to my pants.
I have none.
Hi.
- Hello.
- I'm locked out, please let me in.
- Oh, yeah, for sure.
- Thank you.
Do you notice anything different about me,
while you're at it?
- Uh, no.
- This is not you.
I've never seen you wear a dress before,
this is so cool.
And what is this?
God, this is so (mumbles).
It's hard to not stare at your legs,
but I shouldn't stare at your legs.
- [Tan] Are you objectifying me?
(laughing)
I think I turned a gay man bi.
- Yeah, a little bit.
- A little bit.
So, my girlfriend literally just texted me to ask
whether I'm in the dress already.
I've invited her out for coffee.
Here are my original clothes, and here is my leg
in case you forgot how it looked like.
- Ah, hey.
What's going on?
It's cool.
- [Tan] Leg
- Leg, yeah a little bit of leg.
- [Tan] It's Heaps Of Leg.
- Awe, it's not that much.
It's really nice, actually.
- But when I sit down it shows my entire vagina, basically.
That's what it feels like.
- It's pretty fun, though.
- Totally forgot that I was in a dress,
and then I caught site of my reflection, and I was like,
"Shit, that's right."
She said, "You look really fancy and like you're about
"to walk into a room and just fire everybody."
What a compliment.
Honestly, so far, weeing in a dress has been
my favorite thing that I've ever done
as an individual woman.
It's the end of the day and it's kind of a bummer,
to be honest, Sara, because.
- [Sara] I'm so shocked that you're saying that
'cause you so did not want to do this.
- I know, but the only time I've felt this comfortable
is literally when I wore my pajamas to work.
They're so convenient going to the toilet,
going to the restroom and just getting out of there
within seconds.
Wow, and everyone has been looking me up and down,
checking out my legs.
I'm kind of enjoying that, it's fun.
Someone was like, "It's the first time
"I've seen your ankles," which is pretty funny.
- [Sara] Ankles.
- I can't fault it, apart from a couple of times
it felt like it was riding so far up that it was
almost just at my underwear.
It just reminded me how much of a performance clothing is.
I know it's not that far off from what I normally wear.
It's still black, it's still kind of goth,
but this was a really big deal for me.
I actually, legitimately think I would wear this
to like a casual kind of event.
Maybe like a movie, film opening
or like a nice dinner with a mate.
You often tell yourself that you can't do something,
especially when it comes to clothing or hair color,
hair style, we're like, "Can I pull that off?"
Of course you can pull it off.
I'm boring, I've realized today.
(rhythmic music)