I Wore My First Dress In 20 Years

I Wore My First Dress In 20 Years

– 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)

100 Replies to “I Wore My First Dress In 20 Years”

  1. Tan has a very curvy and feminine body with huge boobs and wide hips and nice legs and somehow her normal clothes completely hide all that and im just astounded

  2. At 4:01 when that dude said "it's strange that I've never seen you wear a dress before" I thought she was gonna answer that she never saw him in a dress either or something like that 😂

  3. Honestly it’s the same for me my family thinks I’m a goth because I like to wear jeans all the time it honestly hurts

  4. To be honest I don't see the problem. Probebly it's because of iam normal man. But I think it's good that you like it

  5. I had to wear a dress for eighth grade promotion and I felt really uncomfortable with that, so I got one that was black with built in shorts underneath but I actually got compliments, which surprised me

  6. 💋Her legs!… her legs, man!!!!. 💘Freaking love her legs, she looks so amazing!!!. If I saw her out walking in that outfit… I would literally STOP to see her. 👀💘💋💋💋💋💋💋

  7. Tan is SO pretty, and her body is so lean and elegant. She can wear whatever she wants and looks gorgeous.

  8. She said "You look really fancy and like you're about to walk into a room and just fire everybody". Suddenly I have a brand new metric upon which to base my appearance.

  9. Who is Tan kidding, she loves the little thigh ash because she has lovely thighs. She was uncomfortable at first but the thigh peek made it more adventurous.

  10. why was i not surprised that the first person she showed on camera while showing off her dress was a flamboyant dude. at the very least its nice to see her embrace and have fun with something more feminine than whats usually her style

  11. it's kind of adorable that she wished she had worn better underwear or wasnt on her period. Like, I literally love wearing dresses when i'm on my period cus i feel like if i bleed through or leak, there wont be a bloody spot on my butt. And since i have thick chubby thighs, I have to wear shorts or leggins under any type of skirt so it doesnt matter if i wear good or bad underwear hahaha the only thing i have to worry about is when the short is too short (but that's cus of my weird size) abd hold my skirt down if its windy and ny skirt looser.

    I used to be SO uncomfortable with dresses, cus they were often too short, my thighs would rub together and hurt, i was insecure about my chubby thighs, i couldnt sit comfortably etc etc

    but now i only just discovered that i really like dresses and skirts….

  12. I’m 13 and the last time i had a dress on was when i was 8, my mom forced me, bc we were going to this party thing. (I hate parties btw) And I’ve always hated wearing dresses and other girly stuff

  13. Oh my gosh ur so beautiful!!! I don’t care if ur in a dress or not, ur so pretty and I wanna be a tom boy too. I’ve already started wearing a lot of my brothers clothes. Most of my friends already think I’m a boy sometimes. 😂💩

  14. I think you have to try on dresses to know how they'll fit. For me, some look okay in pictures on models, but then look ridiculous when I put them on.

  15. As a person who refused to wear dresses for years I totally get this. Props to you its not an easy comfort zone to step out of. That being said I think it helps when you can find the sort of dresses you like and are comfortable with. Instead of those frilly what you think you're supposed to wear dresses. I wear dresses almost every day now. I wear them because I'm lazy, I enjoy the breeze, and I pay for one article of clothing and I have a whole outfit. Super easy..anyway well done.

  16. Man!! i have a humongous crush on Tan…am being soo mean but i just don't want Tan to like dresses….she's dope as a "guy"…tomboy…

  17. "i just turned a gay man bi"
    Well i could say the same with what you did to this straight 14 year old girl for some time now.

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