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September 11, 2025 16 mins

It's Rory's first day at Chilton but it's also the debut of TWO iconic Gilmore Girls outfits! We get to see the chic Chilton uniform for the first time and we experience the chaotic symphony of what Lorelai wears when everything else was at the cleaners. 

How do we feel about the tie-dye/Daisy Dukes/cowboy boots combo?? And how cool is Rory's watch?? 

Plus, we do a deep dive into Jackson's shirt while he argues about the water content of some peaches, right here on Stars Hollow Style!

See omnystudio.com/listener for privacy information.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
I am all in.

Speaker 2 (00:08):
That's you.

Speaker 1 (00:16):
Stars Hollow Style with Easton Allen. Then iHeartRadio podcast.

Speaker 2 (00:22):
Hey, what's up everybody, It's Easton Allen. I am here
on stars Hollow Style. Yes, we are turning the gazebo
of Stars Hollow into the runway. We are diving deep
into the fashion of Gilmore Girls. That is what we
love about this show. This is gonna be a lot
of fun. Okay, we're two weeks into this and I'm

(00:42):
having the time of my life. If you are following
along at home, we're going to go back to season one,
episode two. Okay, this is the Loreleized first day at Chilton.
And here's what we're gonna do people. If you're just
joining us, We're going back to the beginning of Gilmore Girls.
We're going episode by episode to look at all the

(01:02):
great fashion choices that happen in this show. There's some
there's some wild stuff, there's some chic stuff. There are
some great outfits that I want to emulate today. I
know you do too. We're going to pinpoint our favorite ones.
We're gonna maybe highlight some of the bad ones, the
weird ones, and we're just gonna put it under the microscope.

Speaker 1 (01:23):
It's gonna be a lot of fun.

Speaker 2 (01:24):
If you love fashion, if you love Gilmore Girls, if
you love clothes, We're gonna do it all. It's gonna
be a good time here on Star's Hollow Style. Let's
get into this. This is a big episode. Okay, this
is a big episode for some major outfits, and you're
gonna know right away.

Speaker 1 (01:42):
Here's where you know.

Speaker 2 (01:43):
I'm kind of figuring out what we're doing here. I
make the rules. Okay, I know this. Scott's faces on
the podcast start and everything.

Speaker 1 (01:51):
I'm making the rules. I'm deciding how we're gonna do this.

Speaker 2 (01:54):
I think I'm just gonna go beat by beat through
this episode and highlight the outfits that jumped out me,
and we're going to share some thoughts. We're going to
do some analysis here and then we're going to go
back and kind of give it a ranking. Does that
sound good? Shout back at me if you think that's
a good idea. But we're starting off the episode here.

(02:15):
It's it's Rory's first day at Chilton at the private
school and Lorelei, oh goodness, Laura overslept. She woke up late.
She does not have time to get ready. I want
to point out Lorlai's pajamas are great. She's wearing Paul
Frank pajamas. And I don't know if you remember Paul Frank.
It's this adorable little chimpanzee like logo. I love Paul Frank.

(02:38):
I miss Paul Frank. I wish we could see more
of it today. It was great seeing Paul Frank on
those pajamas again.

Speaker 1 (02:45):
But here's the.

Speaker 2 (02:45):
Thing, Lorelei, I mean, man, she's all over the place.
We know this about her. That's why we love her.
She she seemingly got every single piece of clothing dropped
off at the dry cleaners. She woke up late, she
has to get dressed in a hurry. She cannot wear
the suit that she wanted to wear to drop off

(03:07):
Rory for her first day at Chiltern. She can cox
the most wild and unhinged outfit you can possibly conjure
in the world of Gilmore girls. This is an iconic outfit.
And again, go to our Instagram at I Am All
In podcast, We're gonna have all these pictures posted up
there so you can visualize what I'm talking about better. Yet,

(03:27):
put the episode on on Netflix, hit Mute and listen
along with me, fast forward as I go through it.
But this outfit is a key moment in Gilmore Girls.
Loralai wears this like pink tied eye shirt. She's wearing
short denim shorts. I apologize if this isn't the appropriate phrase,

(03:50):
but the daisy duke shorts is how I would describe them,
and cowboy boots. That is what she has decided to
wear to drop her daughter off at this very prestigious,
expensive private school. And I know, listen, people, I go
on the message boards, I go on the reddit's, I
go on the I'm walking around just talking to people
in town about this. I know that this is a

(04:13):
very hot topic. I know that this is a very
controversial moment for Loralai. Is that truly the only outfit
she could come up with to take her daughter to school?

Speaker 1 (04:24):
Probably not. Let's look at the facts here.

Speaker 2 (04:28):
She dropped off all of her suits like her business
attire at the dry cleaners. She has no suits, she
has no slacks, she has no jackets, she has no skirts.
She could have probably found a more appropriate T shirt
and a pair of blue jeans and maybe a pair
of ballet flats to wear to take to take Rory

(04:48):
to school.

Speaker 1 (04:50):
But let's get real here. This is a it's a
TV show.

Speaker 2 (04:54):
It's fun to see her in this really crazy outfit
going to school. It's wild and I love it. Everybody
is noticing the cowboy boots. She's getting a lot of
grief from Emily, from people at school about what time
is the rodeo? You know. And I've always fantasized about
being able to wear short denim shorts and cowboy boots

(05:15):
to a business meeting or to an important moment of
my life. So this is wish fulfillment for me. I
love this outfit. I sign off on it. It's weighing
heavy in my head. And at the same time, while
Lorala is having this wardrobe catastrophe, this wardrobe malfunction, if
you will, Rory is ready to go for Chilton. She

(05:36):
is wearing the uniform. And this is another big moment
in Gilmore Girls. This is a crucial turning point. This
is a nexus nexus event. This is the debut of
the Chiltern uniform. We love the children uniform. It's called this.
This is beautiful like navy blue blazer with the cool
crest on it. Man, I went to public school. People

(05:59):
I wanted to wear a uniform so bad when I
was a kid. I would have loved this that that
crest is so cool. And something that I when I
look at the children uniform that I just love is
how much of an impact it has on popular culture.

Speaker 1 (06:16):
In terms of wardrobe today.

Speaker 2 (06:19):
When you think of like fictional school uniforms, if you
just stop someone on the street, they're gonna say Hogwarts.
That's gonna be the top of mine. But I really
think Chilton is up there. And when we there's an
event that Warner Brothers graciously holds every year and they're
doing it again this year at the Warner Brothers lot

(06:39):
called Holidays Made Here, And I believe Scott will tell
you more about that in the coming weeks. But they
they have They've got a gift a children gift shop
there and you can get all this stuff. You can
get your own uniform.

Speaker 1 (06:52):
It's so cool.

Speaker 2 (06:53):
You can get the blazer with the crest on it,
you can get the plaid skirt. I don't think you
can get the saddle shoes, but that is part of
Rory's outfit as well. I love the saddle shoes. It
throws it back to a time that I love And
there's another part of this outfit that I.

Speaker 1 (07:07):
Really want to highlight here.

Speaker 2 (07:08):
Okay, she's wearing She's wearing this like the school uniform,
this very professional the blazer, the skirt, the plaid skirt.
But she's also got this like very nineties chunky pink watch.

Speaker 1 (07:25):
This like big old watch.

Speaker 2 (07:27):
And I tried to figure out exactly what kind of
watch it is. The best I could come up with
was it. I think it's a Cassio Baby G which
is a version of the G Shock, which is still
a very popular watch today. I believe that is what
Rory's wearing. And the part of the episode where she's
in class and she has to kind of own up

(07:49):
that she smashed Paris' project, the watch stands out like
a sore thumb to me.

Speaker 1 (07:55):
I kind of love it.

Speaker 2 (07:57):
I love that she is like in this really fancy place,
but she's got this like a giant, kind of chunky watch.
It looks like it's almost plastic. It's got some like
metal like protectors on it. It's just very incongruous to
the rest of her outfit. But I really like that.
I think that's really fun. I kind of like when

(08:18):
there's one part of an outfit that goes against the
rest of it and kind of makes you, makes you think,
challenges your perspective a little bit. So we get to
see the children uniform for the first time. After LORIAI
drops Rory off at Chilton, she goes to Luke's. She's
still in this crazy outfit. She goes in there and

(08:39):
Luke is establishing the uniform once again. He's wearing like
a green flannel layered on top of a long sleeve
shirt and his signature backwards hat. I love this flannel
in particular more than the first episode because I think
this is a Pendleton. I can't confirm that, but I
think this is a Pendleton flannel shirt. It's probably wool.

(09:02):
I'm you guys, come closer, get really close to the speaker.
I'm really excited because I'm pretty sure I have this
exact same Pendleton in my closet right now, and I
did not buy it because Luke has it. I saw
that on screen and I became the Leonardo DiCaprio meme
pointing at the screen.

Speaker 1 (09:20):
I jumped up.

Speaker 2 (09:20):
I think I had that same flannel. Luke and I
am basically the same person. It's so fun, so exciting,
and it looks great on and really brings out his eyes.

Speaker 1 (09:29):
I love that.

Speaker 2 (09:30):
I love that flannel shirt. You know, as we go
through the series here, we're gonna Luke does not deviate
much from his outfits, but when he does, even if
it's just a thing in terms of a different colored flannel,
we're gonna highlight it, We're gonna celebrate it, and we're
going to raise it up. There's another really iconic outfit
in this episode that stood out to me on our

(09:51):
good friend Jackson, and we are going to talk about
that after these commercials.

Speaker 1 (09:55):
Please stick around. I'm begging you.

Speaker 2 (10:06):
Hey, everybody, thanks for listening to those commercials. I know
you listen to every single one, and you're gonna buy
all those products.

Speaker 1 (10:11):
Right right, You're gonna spend all your money here.

Speaker 2 (10:14):
Right anyway, This is the Star's Hollow style. My name
is Easton Allen. Thanks to Scott Patterson for giving me
the keys to his car.

Speaker 1 (10:21):
Where was I? All right?

Speaker 2 (10:22):
We were talking about one of my favorite outfits of
this episode. We Laura I is at the inn. She
walks in on Souki and Jackson. They're talking about the
quality of the peaches they're too watery. They're in the
middle of an argument and Jackson is wearing this outfit
that I love.

Speaker 1 (10:38):
Okay, that shit edited nicely.

Speaker 2 (10:42):
Another outfit in this episode that I want to highlight
is it's back at the Inn, Laura. I walks in
on Souki and Jackson arguing about the quality of the
peaches in the kitchen, and this is we get to
see Jackson's outfit and he's got a very cool look
at tells you a lot about his character.

Speaker 1 (11:01):
He's wearing.

Speaker 2 (11:02):
I don't know how else to describe this beanie besides shallow.
It's a beanie that does not cover most of his skull.
It's like just the northern hemisphere. It doesn't even reach
his ears. It's very very short beanie. This was very
popular in northern California in the twenty tens. I saw
a lot of guys, a lot of hipsters.

Speaker 1 (11:24):
Wearing this type of beanie.

Speaker 2 (11:25):
And I am not from a cold climate. I'm not
a beanie guy, but I would see a lot of
guys doing this, And this feels like a more versatile
thing if you're not if it's not very cold outside,
you just want to warm the very top of your head.
It kind of looks silly to me, but Jackson pulls
it off. He's also wearing a T shirt that I
spent a lot of time staring at today. I canceled

(11:49):
all my meetings, I canceled plans with friends. I locked
myself in my room. I projected this on a big
screen and I just stared at this T shirt that
Jackson's wearing.

Speaker 1 (11:58):
He's wearing a T shirt.

Speaker 2 (11:59):
It's like it's a circular emblem and it says it's faded.
It's clearly like a vintage thing. The costume designer probably
got this at a vintage store. It says planet Watch,
and it's a circular logo and it's called like a
Captain Planet looking globe with what looks like binoculars. Again,
go to our Instagram at iaml In podcast and you

(12:21):
can see this for yourself. Okay, allow me a little
bit of time to be a nerd for just a second.
I was trying to figure out what Planet Watch was like.
Is this a band the Jackson likes, Is this a
green peace kind of thing?

Speaker 1 (12:34):
What is this?

Speaker 2 (12:35):
The only result I could really find from Planet Watch
is in the world of DC comics, there's like some
In the newest Superman movie, the one that just came
out this year, the bad guy has this team called
Planet Watch that works with a government or whatever, and
I think that that was a thing in the comic

(12:55):
books too. Jackson seems like the type of guy that
would probably that would wrap a very obscure DC comics team.
But also, I mean, I don't know what this is.
And that's something that I enjoy is that as we
get to know Jackson as a character, what is Planet Watch?

Speaker 1 (13:09):
What is he into?

Speaker 2 (13:10):
Is he? What kind of guy is he? Why is
he wearing this jug head looking crown hat thing. It's exciting.
But Planet Watch is now on my mind and hopefully
it is on yours too. It has really captivated my imagination.
I spent a long time looking for that shirt and

(13:30):
I was not able to find it. So, you know,
the rest of the episode is there's a lot of chiltern.
Obviously this is there for her first day, so there's
a lot of chilt in uniforms. We get to see
our boy chat Michael Murray. He's in a really cool
looking blazer with the tie and nothing really to write
home about. But I want to I want to go back,

(13:55):
and let's just take another moment to highlight and celebrate
the iconic outfits from this episode. I think, I mean,
there's two really that we're we're talking about here. This
is the the Rory over sleeping. All her clothes are
at the dry clear Everything she owns is at the
dry cleaners. Every single piece of clothing, and so she
has to wear the pink tight I shirt, the short

(14:18):
jean shorts, and the cowboy boots. Looks so cool. I
know that she was embarrassed by it. I know it's
like not very appropriate to drop your daughter off at
a at a fancy school dressed like that.

Speaker 1 (14:30):
I love it. I think it's rad as hell. It's
great that that is an outfit.

Speaker 2 (14:35):
I think people dress up like this for Halloween, Like
this is still an outfit that people associate with Rory
here in episode two. I love that outfit that really stands,
stands true and tall to me, and Rory's Chilten uniform.
This is the first time we get to see it.
It's so cute. I love the I love the saddle shoes.
I love those saddle shoes. I love the pairing of
the crazy giant g shock watch. It's such a great

(15:00):
look and I'm excited to see these outfits evolve as
the as the season goes on. Thanks for falling along, everybody.
This is Stars Hollow Style. We will do this again
next week and if you want to join us, we're
doing season one, episode three. The episode title kill me Now,
something you might be saying after listening to this, No,

(15:21):
I'm just kidding.

Speaker 1 (15:22):
The episode title kill me Now.

Speaker 2 (15:24):
And we're gonna go through those iconic outfits as well.
We're gonna dive into them, we're gonna analyze them. It's
gonna be a lot of fun. So let's do it again.
Y'all look great. Don't forget that, everybody, and don't forget

(16:05):
Follow us on Instagram at I Am All In podcast
and email us at Gilmore at iHeartRadio dot com.
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Hosts And Creators

Amy Sugarman

Amy Sugarman

Danielle Romo

Danielle Romo

Scott Patterson

Scott Patterson

Tara Soudbaksh

Tara Soudbaksh

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