- [Interviewer] Will you take your blindfold off?
- Yeah.
Oh
(laughter)
Oh hey.
I know one of you.
I like where this is going.
(laughs)
(slow music)
What am I guessing?
- [Interviewer] What do you think?
- Size of something? I don't know.
(laughter)
- [Interviewer] You're gonna match outfit to person.
- Oh. So you're all in your undies.
(laughter)
Cute.
- [Interviewer] What's your style?
- I went kind of simple for the filming.
But lately I've been working on militant faggot.
So my kind of way of resisting all this bullshit
is to dress as like militaristic as I can
and like faggot up.
- Yes.
- Let's do this.
- [Interviewer] You ready to start guessing?
- Yeah.
(wheels rolling)
Well I'm seeing a nice... what appears to be a romp them.
I'm not trying to be ageist,
but yeah maybe a little younger. Come on up, pal.
Richard I pick this outfit for you
because you have a kick-ass body
so I feel like you're not afraid to show your hips,
your legs. Try it on.
- Alright.
(slow music)
- You look really cute. There we go.
(slow music)
(wheels rolling)
- [Interviewer] Tell me about this outfit.
- It's got like a nice vintage look, I like the cuffed
detail on these sleeves.
It looks like kind of a more dated shirt, maybe 80s.
I want to go with you. (claps)
- Okay.
- Yeah. I chose you because of your luscious,
flowing curly hair. I also think this cut would fit
your shoulders very nice.
(slow music)
- Yeah, I like it.
(slow music)
Hmm.
They're wearing athletic wear with like a flowy jumper.
So I'm going to say this person is very resourceful.
I feel like I would see you in this.
- Yeah?
- Yeah. Come on up. High functioning, minimalistic (laughs)
not functioning very well.
(slow music)
I see so much color. I mean this could all very well
be thrifted, but it could also be like off the rack.
I'm gonna go with you (claps). I like this on you.
(laughter)
You just have like a really bright face and a bright smile,
- Aw. Thank you.
- you've really got kind eyes.
Do you want to try her on?
- Yeah.
(slow music)
(disappointing sound)
- (gasps)
- I'm gonna wear it another way.
- (gasps)
(metal music)
(laughter)
(slow music)
- This looks like some nice business casual.
One could wear to the office.
Nice buttoned down from Express.
Lets see if the tie is from Express too.
Oh, J.Crew. Okay. (claps)
I'm gonna go with you. You have a little bit of makeup on,
you want to look professional and put together.
Yeah lets see it on.
- Okay.
(slow music)
- That is a six figured salary if I've ever seen one.
(laughter)
(slow music)
(light music)
- This is cute. This looks like an outfit that falls under
my favorite term, studied negligence.
You look like you haven't been trying
but you definitely like put a lot of thought
into what you're wearing. Let's see.
I got you baby.
- Why am I wearing this?
- It's complex, it's got layers, you're not afraid to
like queer it up a little.
(slow music)
This is really fun. We've got a two piece green suit here.
(laughter) - Want to try the suit on?
(laughter)
come on up. You have broad shoulders
and I feel like this jacket will compliment those
broad shoulders quite nicely.
(slow music)
(zips fly)
- Wow this person has taste. Oh.
- Hey. - We just made eye contact.
(laughter)
- Come on up. This is a look that would look really good
on your body. I want to see this on you.
- Alright.
(slow music)
- [Interviewer] With a show of hands
who did Timmy get right? Okay take a look.
(laughter)
- Are you fucking kidding me?
(everyone laughs)
- I'm the worst. You two threw me curve balls.
- [Interviewer] They're gonna get changed
into their right outfit.
- Oh okay.
- [Interviewer] How was that, Timmy?
- That was fun.
Oh okay.
- Makes sense now?
- Awesome. Yeah.
So we'll start with...
- Dave.
- So tell me about this.
- Well...
- First of all, did you make it?
- I did.
- Awesome.
- It was... good observation.
- What motivates this style for you.
- I like alternative fashion.
- [Timmy] Have you sewn long?
- Yeah, off and on for about 10 years.
- [Timmy] Oh cool.
- Working on kind of developing a beachwear line.
- [Timmy] Cool. Well, thank you.
- Yup, thank you.
- Alyssa
- Alyssa, that's right. This is so cute.
- Just for the record, none of this is thrifted.
(laughter)
- I thought so.
- I like to push the envelope. I like to mix high and low.
For this instance the sewing bag is high end.
The cashmere is also a high end sweater.
And then this is from Anthropologie for $1.50.
So it's like high and low, that's how I shop.
- Yeah. $1.50 is really low.
(Alyssa laughs)
- I'm kidding.
(loud smack of bag)
(laughter)
(clapping)
- Hello. Hello
- What's up?
- How are you?
(both laugh)
Tell me about your style.
- My style is ever changing but I like to mix elements;
masculine, feminine, utilitarian, flowy.
I love taking things from straight culture.
This is like a biking top, and just like making them gay.
- [Interviewer] Thank you.
- Hey.
- Tell me about your style Jade.
- I think my style changes a lot. I think today I'm more
masculine, and sometimes it can be super feminine and sexy.
So, it just depends on my mood.
- [Timmy] Yeah, I was thrown by your makeup
I'm not gonna lie.
- Yeah.
- Like I was expecting a little more femininity
in your attire but this is like my favorite thing
in the world. Again, you like juxtapose those things
and you like mash it all together.
- Yeah.
- So, tell me about your style.
- Well I do (laughs) have my moments of dressing
more feminine versus masculine but overall
like within smock look. (laughs)
- So smocky.
(laughs)
- That's me.
- Smocks for days.
- Hi.
- Hi. I like your romper it's really cute.
- Thank you.
- Yeah, tell me about your style.
- My style is casual, prints, floral, color
but I also like to amp it up a little.
- Come on up Stephanie, I remembered yours.
- Aw, thank you.
- Because you look like my aunt Stephanie.
- Really?
- And trust me she's a total milf.
Can I say that about my aunt?
(laughter)
- So tell me about your style.
- My style is fun, spunky and a bit unexpected.
These are my husbands tie and shirt.
- Oh, cute.
- And then I just put it with this skirt
to just make it more fun.
- Do you swap clothes with him a lot.
- I actually do.
- Does he ever wear your clothes?
- No. Sometimes a t-shirt.
- What's his name?
- Greg.
- Step it up Greg.
(laughter) (clapping)
- Cool, thank you.
- Come on up.
- What up? What up?
- Hey, this looks really good.
- I appreciate that.
- It's tailored for your body, it looks really great.
- My style is classic modern. So thus I play with
lots of colors and bold patterns.
- [Timmy] How many suits do you own?
- Probably, 10.
- Oh, nice.
(clapping)
- [Interviewer] Is Timmy worth a group hug, everybody?
(unanimously) Yes
(clapping) - He has to do a runway walk.
- Oh.
- Do I?
Okay.
(slow music)