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Stars Hollow Style: Work It Lorelai! (S2 E18 “Back in the Saddle Again”)
Freitag, 10. Juli 2026 · 17 min
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Get ready for some ALL TIME great Lorelai work outfits in this episode! We get a glimpse of the fashion icon Giselle and a three-way showdown of looks in downtown Stars Hollow from Rory, Lane and Dean.
Plus, a favorite Rory dress from season 1 makes a return!
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I am all in follow I guess you Stars Hollow Style with Easton Allen, an iHeartRadio podcast for all the little boys and girls out there that have longed and wished for a podcast just about the fashion of Gilmore Girls. This is for you. Hey, it's Easton Allen. This is Stars Hollow Style. Thank you so much for joining us.
This week, we're talking about season two, episode eighteen, Back in this Saddle again. What an episode, you guys. This is so fun to go back and look at Gilmore Girls through such a narrow lens, just the clothes, and this episode had some fantastic looks. I'll be honest, I can find myself being pretty snarchy when I do this.
That's just my nature. I'm sorry, It's who I am. And part of the reason we love Gilmour Girls. And one of the many quirks of this show is the fashion we see is often baffling, and we are not afraid to point that out. And sometimes I can be kind of you know, I can be a little harsh, but that's I don't know, I'm just having fun, you know whatever. This episode be prepared for sincerity. There's not a lot to make fun of here, and there's not a lot to snicker about. We're just going to appreciate good fashion in this episode. Would you like to join me?
The cold open will start there. That's a good place to start at the beginning. Loralai and Rory look great. But I want to comment on Emily's Saint John suit. Another one. She has a closet full of these, and this one looks great. This is it's like it's navy, and then she's got these like beaded accents on the zipper going down the middle and on the pockets on her jacket. It kind of makes like a cross pattern with these beads. I thought it looked great. I really liked that suit. Emily wears so much Saint John, and I always want to point out when it's something remarkable.
In this case, it was after the intro, Laurel and Rory go to Luke's Diner, where they're shocked to see a new special on the chalkboard. Laurels wearing a light blue button up shirt with a white collar and white cuffs contrasting there. I used to see businessmen and you know, some mobsters, but I would see businessmen in like movies where this kind of thing all the time in the nineties and the two thousands, like like a dark blue or a light blue, then like stark white cuffs and collar that I thought it was really cool. And to me, I remember being a kid watching seeing a guy in that in that kind of shirt, saying, Wow, that looks expensive.
That looks so expensive. And Laurelei's got that same classy look here in Luke's Diner. I really liked it. Dean joins them. Do you guys remember this episode that Dean is at his whiniest and most pathetic. I think in this episode it's a bummer to watch anyway. Dean joins them. He's wearing a soft, comfy looking red sweater layered over a gray T shirt and then a tiny, tiny chain.
Pretty standard Dean looks in this moment at Luke Steiner. Then we'll go to the inn looking at the wedding invitations for Susie Saint James, and we get to go on an adventure with Soki. Here we get to see and test the limits of what a Paisley bandana can be. And in this world you can be anything you set your mind to, and right here we get to see that the Paisley bandana has taken over Soki's entire life force in multiple formats. She's got a black bandana Paisley bandana wrapped around her hair. But then her chef's outfit.
We love tween out her sh outfits. We talked about that a lot. This one is great. We really, we really admire it. And this is because before we've seen like, you know, rose patterns or stuff like that. This moment, she's wearing a navy, long sleeved chef shirt with a pattern of You guys, maybe I'm wrong here, it looked like smaller bandanas on her chef's outfit. It was like a pattern of squares that each had a different kind of design. It could have been tiles, I guess, like like, you know, like cool Spanish tiles, but to me, there's a couple of those on there that are just full blown regular Paisley bandanas. So it was like a shirt with bandanas printed on it. I thought it was fun.
I really liked it. It was really it's neat. We see Souki wears so much Paisley bandana stuff, especially when she's at work, So I just thought that was that was fun. It's like when you see a T shirt with a T shirt printed on it, it's cool. It's it's not normal, all right. Next up, we'll go to Downtown Stars Hollow. Rory and Lane are walking down the street.
They're talking about their professional future when they get approached by Classic Whiney Dean. Okay, so we got a trio here on the street and we're gonna go through their outfits. I'm gonna list them in order of who was best dressed to worst dressed. So taking the number one spot, Lane, I liked her outfit the best. She is best dressed here in this moment on the streets. She's wearing a dark indigo denim jacket over a white button up shirt with like a nineties style pastel swatch pattern on it.
It was just like looking just like you know, blotches of like pastel colored paint. I liked it. That was really cool. She's paired this with charcoal pants and black platform shoes. Lane usually looks really good and this is no different. I really liked this outfit. I just I thought it showed off her personality a lot, and I thought it looked good on her. I think the colors were very complimentary to her hair and the rest of how she carries herself. Next up is Dean in the number two spot. He is so sad about Rory not watching his softball game, and he enters this moment wearing a gray sweater with a black stripe down the sleeves.
He loves these kind of sweaters. He's like nineties looking long sleeve sweaters. He wears them almost exclusively, and that's layered over a kind of a baggy shirt that you can see it bunching up under the collar. And he pulls off a pretty magical moment right here, if you will go back and watch this. When Dean enters, he's got like a green I think it's a pukashell necklace. Again, Dean loves his jewelry, he loves his accessories. He's got a green pukashell looking necklace. It's kind of like tucked under the collar of his sweater. When he sees them on the street and approaches them and he walks up, it's still kind of like tucked under the collar. A little bit, we cut to Rory and Lane, we cut
back to Dean. That necklace is out on display, it's over the collar. It's where it's supposed to be. It's sitting on top of his sweater. He says, this piece. We go back to Rory and Lane back to Dean, it's tucked under the collar again. Oopsie oopsy the magical self moving necklace. I guess, you know, obviously this is a continuity problem, but also I guess it's not unrealistic that Dean could have been nervously fidgeting with his necklace.
He doesn't seem like a guy that does that. So I'm just gonna say, Wow, major blunder there. Hope someone got fired for that one. Anyway. Lastly, in this scene, the worst dress of the trio Rory Gilmore. She is wearing a blue longsleeve button up shirt with what I like to call a lazy plaid pattern on the front.
It's just on the front, there's nothing on the back, and it's like plaid kind of straped design that looks like it looks like if you look at a plaid image and then zoom out, like it's like you enlarge everything in the zoom out if that makes sense. It's a or actually or maybe zoom in. Yeah, it's like if you were an ant and you're crawling on top of a plaid shirt, it would look like this. It's everything's really big and spaced far apart, so it's not like a typical plaid. It's just like the just the stripes and then big blocks of contrasting color. And if you look at the bottom button on this sweater as you're watching along with me, you can see the edges of the sweater, you know, sweater shirt, whatever it is,
start to flare out a little bit. It makes me think that this doesn't really fit her that well, it doesn't fit the right way. So I don't love what she's wearing here. She's also wearing these pants with a button fly that that's a really long, like, just so many buttons going on in this rory outfit. I do not like it. Also, I just want to say, you guys, this is my first week doing this on Hulu, watching the show on Hulu. I don't know if you guys have been watching since the Netflix the end of the Netflix license, but I just switched to Hulu for this episode.
I don't like it. I did not have a fun experience. Just to you know, I watched the show for the podcast, and I'll pause it when I want to look at the outfits, and when you pause it, it like all the Hulu nonsense shows up on the screen and you can't get it to go away. It's so annoying, you know, because I need full screen, I need high definition. Anyway, I'm really sad about it not be on Netflix anymore.
It's a bummer, but you know we got Hulu. Thank goad. Okay, next up, we're This episode is a great run of incredible lore light workoutfits. She does not always hit it, but this episode she's firing on all cylinders. We're going to talk about that after these words. What do they fuck? Hey, folks, summertime can be hard for all of us. So that's why I'm given better help a try. This is Easton from Stars holl Style. I'm just kidding. We're back. The commercials have ended. That was a joke. I'm goofing around.
No more commercials. This is just pure uncut content. Let's get back to it. We're talking about season two, episode eighteen. Back in the saddle again, which is where we are in this episode. So before the break, we were talking about Lorelei's workout fits, and we're going back to the inn here at this point, in the episode LORELEI wearing a blue blouse with these like raised dots all over the all over it. It's like a very small you know, I'd say, a like a sixteen live an inch orbs raised all over her blouse. I liked it. It was like a three D poga doot and it's got these frilly cuffs. Very fun. I was looking at this shirt and it's blue. Toont if, I said, the color, it's blue, that's very important. This shirt, to me felt like she
loves those tuxedo shirts. We talk about that a lot. She always wears those in like a formal situation or if she wants to impress people. She wears a work a lot too. Those like for roughly tuxedo shirts. This feels like a toned down version of that. This feels like she wants to get that same kind of vibe and fun, but it's much less. It's much more subtle.
Like the frillly sleeves I think are easier, are easier for like a normal person to swallow than the ruffles going up the middle like on the where the buttons are. I liked this shirt a lot. I think it was very fun and a nice little kind of a nice departure from what she normally does. Now we're going to the Gilmour Hill House now, where Lorela's reading the Motley Cruz book and Rory's coming home from her travels checking the answering machine. Not an important fashion moment here, but I just want to point out this scene because as Rory is skipping through the messages from Dean, the tone they chose for the next message sound It just sounded just like when you get a coin in Mario Brothers on the Nintendo, like the original one. But this is
fun to hear that anyway. That's all. I'm sorry. Back to fashion stuff, Okay, I got to keep in my lane. I stay in my lane. This is in a sound effects podcast. It's fashion. It's Gilmore Girls starts all style. Now let's go back to the inn. We're hanging a U turn. We're going back to the Dragonfly in and or sorry, the Independence in. Oh my god, I'm getting ahead of myself. Some fantastic looks in this scene from Lorley and Giselle, Michel's mother who was there visiting Horson.
Lorelay's wearing this black scoop neck top with an off white like flower pattern, these really big flowers and long stems. I really liked it. The flowers themselves felt like something you'd see on a framed print in someone's house in like the eighties. It was a really cool design. I wish I tried to find it and I couldn't figure it out. I really liked it. Though. I liked it a lot. It feels like if you went to like a really chic like lawyer's apartment in like nineteen eighty six, they'd have this like framed in the living room. I really liked this shirt or this blouse on Laura LII.
And then Giselle is wearing a hot pink jackawed skirt and blazer. Combo had this like raised kind of pattern on the On the blazer it looks like tropical leaves, kind of like almost like like palm fronds. It was really hard to tell because it's the same color as the as the rest of the blazer, so it's it was hard to see, but it looked kind of like Miami ish. Very fun though. I just love the hot pink.
It looked great on her. Her hair look great in this scene. Giselle's an icon so so chic. I want to be just like her. Uh. Later on, we're staying at the end, We're staying there, but we're gonna skip ahead in the episode a little bit. We're in the kitchen and Michelle confronts Laurlai about how she leaked his lack of carbs to his mother, and Lourally is wearing a red pin stripe button up shirt. Another one looks great.
It was untucked and it thought it was nice and nice and can but still like I'm at work, I'm on the job, I'm the manager. I really liked it. I liked this red button up pinstripe that Laura's got going on. And then we're gonna close out the episode here at Friday night dinner, Loura wearing the same outfit she's got from works. It's a red the red pin stripe button up. She just put a coat on to go to dinner with her parents. Rory, though, wearing a very nice black dress. She's got a red coat on, and when she takes it off, you get to see this nice black dress with like stemmed flowers on it.
You know, the second flooral experience we've had in this episode from m gilmore. We saw this dress before back in season one, episode three, So very fun to see it return. I really liked it. I was having some trouble figuring out who it was, so I called in a favor. I called my friend Melissa at ten percent caffeine.
She she of course, it was crazy. I was like, I was texting her and before I could finish writing the message, she just says, oh, it's Anna Sweet, like she just immediately as soon as I asked if she had the answer, it's an Anna Sweet dress. There was one on Deep Pop. The listing is gone or else I would link it for you, so I'll be on the lookout for this dress. I really liked it. I liked it a lot. I think she looked so good. Here.
That's it, you guys. Those are all the outfits of note in season two, episode eighteen, Back in the Saddle again. Let's go through and do our best and worst of the entire episode. I know we did a mini version of this on the street in Stars Hollow, but let's do it overall. I think the worst outfit in this scene in this episode, in this episode, the worst outfit, you know, I gotta I'm sorry. She's got two trophies now, Rory walking with Lane. I really did not like the lazy plaid. I didn't like the way it fits. I didn't like all the buttons on her pants. That's my least favorite outfit. My favorite outfit, it's got to be Laura Lei's white floral scoop neck top she was wearing at the end when she's talking to Giselle. I really
love that top. I thought it was great. It was hard. That was a toss up. I liked that. I really like the dress that we saw on Rory at the Friday night dinner at the end. It's a great dress, such a great dress. This was a great episode for fashion, so much fun outfits to look at. I hope you guys go on Hulu or you know wherever else, pull out your DVDs and and rewatch this episode and follow along next week. We're doing this again. I can count upwards.
It is season two, episode nineteen. Teach me tonight. Until then, you you you the listener, You look so good. Don't you forget that? Everybody, and don't forget Follow us on Instagram at I Am all In podcast and email us at Gilmore at iHeartRadio dot com.