- Would you prefer to be a potato sack or a pharaoh?
- I feel that my chest is a little bit bigger
than I would like it to be.
It definitely influences the kind of shirts I pick out.
The shirt I'm wearing now is fit in a way
that you can't really see an outline of my chest
and that's the most important thing to me.
- It's not that I'm necessarily afraid of crop tops.
I love crop tops.
As I got older I kind of stopped working out as much
and kind of got a little bit of a stomach.
- It's natural for some guys to have chests
that are a little bit larger.
- I have this term
that I would always explain to my friends.
I'm straight-skinny.
I'm gay-fat.
There's not really a space
for guys who are kind of maybe just in between.
- My goal for this week is
to be a little bit more comfortable in my own skin.
- I'm expecting by the end of this
to be completely 100% confident in my body.
(laughs) Oh, god.
- This is the most bearing, the most shortest.
I want you to do it first
so that we rip you out of your comfort zone immediately.
- Okay.
- This is the front.
- That's the front.
- So, if you're insecure, we will all see.
- This does not look like it's from like this decade
or the last one or the one before that.
- Wow, that is a lot of stomach.
- This is not a shirt.
- I don't think I'd like this after a big Italian meal.
- This is just very shiny.
- Is this how Gaga feels?
Let's go show people my stomach.
What do you guys thing of my crop top?
- I'm headed to a wig and hat party.
So, I felt like this was the best time
to dive in heard-first.
I'm going to drink until I forget what I'm wearing.
So, I had a couple comments on my outfit.
One friend said that they
actually really liked the see-through tank top.
And the other friend said
that I looked like a Pokémon trainer.
I'm taking both of those as compliments.
- I'm a little hung over from last night.
Even though, it was a pretty queer-friendly club,
I felt a little more self-conscious than I usually did.
As cheesy as it sounds,
it doesn't really matter what you're wearing.
It's more of how you present yourself.
My confidence was the determining factor
of the attention I was getting.
And so I think going forward into this week,
I'm gonna hold on to that.
I don't think anything in my life has prepared me for this.
Tommy Pickles here we come.
- Today I am a pharaoh.
The past two wearing clothes
that very much showed what it is
that I usually normally like to mask.
I feel good.
- Seattle.
Venice Beach.
I mean, why am I even wearing a shirt?
Alright, so I'm about to go
into my first public place in this outfit.
I think this is probably going to be the biggest test
of my confidence.
Here we go!
Got my stuff from the store
and, I don't know.
I didn't really feel like anyone was looking me weird.
Honestly, they were probably just more confused
with the nature of this outfit.
(hums Funeral March by Chopin)
- It's day five and I'm wearing the uncle shirt,
which is made of silk, a material I never wear.
- What in God's name?
- I'm feeling okay about it other than the fact
that I look way to festive to be going to Target.
After wearing that see-through tank, I feel just fine.
- Alright, so we just saw a play.
Say hello, Mia.
- Hello.
- I'm not gonna lie.
I had my sweater on the entire time.
- I'm wearing the dad polo and the Dave jacket.
The more I wear these clothes, the more I realize
that I pay a lot more attention to these things
than anyone else does.
- I don't know how people wear
half of a shirt on the regular.
That's crazy.
You ladies ...
- But for fashion we do it.
- Women make sacrifices.
- I am ready for this challenge to be over
and for me to get back to wearing my own clothes.
After this week's challenge,
I definitely feel less insecure
about my chest and my body in general.
- I think that I feel a lot more confident
in my body after this week.
- To anyone else struggling with body insecurity,
I think it's just important to remember
that it's really something
that a lot of people struggle with.
I think it's empowering to know that you're not in it alone.
- People are more focused on themselves
than they are on what is on your body.
And people who are focused on your body,
fuck 'em.
Fuck 'em.