‘Gilmore Girls’: The 11 Best Fashion Moments

Accessorized with 10 boxes of tissues.
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Accessorized with 10 boxes of tissues.
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Hearing that Netflix plans to stream all seven seasons of “Gilmore Girls” starting October 1 might just be the BEST NEWS EVER. (Even though I watched the show when it aired from 2000 to 2006 and about five more times in random order when ABC Family continuously re-ran it.) The always-awesome Lauren Graham, the "mother and daughter as best friends" storyline, the pop culture-filled witty banter and a loveably quirky supporting cast just never get old.

But we also need to talk about the fashion on the show. Yes, fashion was everywhere -- for instance, Kirk’s ever-changing menswear steez (cuz he had a lot of jobs to dress for), Miss Patty’s theatrical outerwear, Richard and Emily Gilmore’s near “Downton Abbey”-levels of Friday night dinner attire and Lorelai’s “Sex and the City” outfits, as described by Emily in a surprisingly aware moment for the matriarch. But some style moments are not only memorable, but also integral to major plot points leading to -- more often than not -- a colossal cry session. So grab a box of Kleenex and take a look:

Lorelai’s Take-Your-Daughter-to-School Outfit

(Also known as the “laundry day” ensemble.) So Lorelai oversleeps on Rory’s first day at Chilton and -- seeing that she’s so domestic -- has no clean clothes to wear. So clearly Lorelai had to go with a pink tie-dye baby tee, distressed denim cut-offs and cowboy boots, with a duster coat thrown over for modesty’s sake. Now this look would totally be street style bait these days for sure, but not so much for taking your daughter to day one of posh prep school, a meeting with crusty Headmaster Charleston, and definitely not for a surprise appearance by perennially Chanel-clad grandma, Emily.

Rory’s First Chilton Dance Homemade Dress

In a pre-P.S. I Made This Stars Hollow, the multi-skilled Lorelai makes Rory a damn good dress for her first dance at Chilton. (None of that “Pretty in Pink” DIY stuff here.) The off-the-shoulder, fit-and-flare creation served as a catalyst for a few important moments in the storyline. First, while still on the dressform, the dress “attacks” Lorelai thereby causing temporary back spasms. When Emily comes over to see Rory off -- mistaking the adorable frock for a store-bought one -- she decides to stay over and nurse Lorelai, which made for a few short-lived touching mother-daughter moments (mushed banana on toast?). Rory, in said dress, makes her way to the Chilton dance, escorted by her dishy, but dopey townie boyfriend, Dean. (And she pulls a Shailene Woodley by taking her heels off early on in the evening.) Her snooty mean girl classmates are actually quite impressed by her homemade look and a hot (and appropriately named) Tristan can’t resist taunting her, again, and ends up starting a fight with Dean. Oh, and Rory and Dean accidentally stay out all night because they fall asleep while… reading a book, which she could actually fit into her roomy party purse. Blame it all on the dress.

Luke’s Baseball Cap

Lorelai’s grumpy on and off-again love interest slash local diner owner was rarely seen without his trusty backwards baseball cap. In a way, the hat became a symbol of the It couple’s dating status. He started out the first season with a well-worn brown cap until Lorelai gifted him with a bright blue one -- aw, she must like him -- and he continued wearing the new one going forward. Well, except for that time Luke and Lorelai broke off their engagement (ugh, April and, oh no, Christopher) and he opted for a mourning-style black baseball cap. And don’t forget that time he forewent headwear all together and wore a suit and tie for Richard and Emily’s vow renewal ceremony. That did not go well. So lesson learned: Luke should always wear a blue cap and let’s just throw in his cozy flannel and manly army parka for good measure.

Luke's infamous cap. Photo by Warner Bros./Getty Images

Luke's infamous cap. Photo by Warner Bros./Getty Images

Lorelai and Rory’s Dance Marathon Dresses

“Dancing With the Stars,” what? In this absolutely epic episode, Lorelai is hell-bent on beating quadruple champ Kirk (I mean, what can’t this guy do?) in the annual 24-hour dance marathon and enlists Rory as her partner. So clearly they must dress the part. (Seriously, does Stars Hollow have the best costume shop ever or what?) The duo’s costumes are on point: Rory in an adorable red polka dot button-front dress and Lorelai in a how-you-doin’-Luke sweetheart neckline halter number and a pair of faulty dancing shoes. When Lorelai runs off to fix her broken heel, Dean steps in to dance with Rory -- who’s been swooning over Luke’s nephew Jess since he rolled into town with his rebel without a cause outfits and perfectly mussed hair. To make a long (but really good) story short, Dean dumps Rory on the dancefloor. If only Lorelai wore flats.

Rory’s Stellar Costume Collection

Speaking of... During her college years, Rory rocked some serious costume game, which usually made a timely appearance during a pivotal point in her relationship with the irresistibly smarmy -- and filthy rich -- love interest Logan Huntzberger. Let’s start with when she infiltrated Logan’s Skull and Crossbones-ish “Life and Death Brigade” glamping excursion. While wearing a Grace Kelly-ish ball gown and carrying a Mary Poppins-esque parasol, she jumped off of a tall landing along with tuxedo-clad Logan and his equally well turned out bros.

For exhibit B, you have Rory’s spot-on Gogo Yubari ensemble for Finn’s Quentin Tarantino-themed birthday party. Granted, she might have recycled her Chilton uniform for her “Kill Bill” character’s outfit, but whatever works to make Logan jealous (or maybe it showing up with a fake blood stained dude named Robert really did the trick).

Of course, there’s Rory’s perfectly tailored Women’s Army Corps jacket, skirt, and hat ensemble for the USO-themed DAR party she organized while on hiatus from Yale. (Kudos to the beauty stylists for the bouncy ‘40s curls and flawless red lip, too). While perfectly clad for the occasion, Rory sees Logan’s asshole dad Mitchum Huntzberger for the first time since her former boss basically crushed her soul during her newspaper internship.

While on the Mitchum subject: He orders Logan to London right after graduation, so Rory sends her boyf off with -- duh -- another theme party. She goes literal this time, with a London motif. I’m not totally understanding Rory’s interpretation of Old Blighty with her red and white collared dress; it feels a little more Orphan Annie to me, plus her attempt at a British accent was a little bit Anne Hathaway in One Day, too. (“Hellow Gov’nah.”) But hey, she looks fantastic with bangs and it’s the effort that counts.

Rory's military look. Photo by Warner Bros./Getty Images

Rory's military look. Photo by Warner Bros./Getty Images

Rory’s Chaste Spring Break Swimsuit

No Ipanema-ready string bikini for Rory on her first ever Florida spring break, along with a motley crew of geeky Glen, jock roommate Janet, and an even more covered-up Paris. (Love you, Paris.) Even Lorelei questions Rory’s choice of modest swimwear, suggesting that maybe her daughter pick up a more festive piece along the way. (Guess the younger Gilmore wouldn’t be into something like this.) Rory insists that her suit is “fine,” as Lorelei retorts, “No, sure it is. It’s nice to be able to go from the beach to the mosque without having to change.”

Rory Had a Birkin Bag Before Kim Kardashian

That time Logan gave his earnestly clueless girlfriend a plush pink HERMÈS BIRKIN BAG and Rory—bless her—referred to it as “a purse.” Logan then verbalizes the words that I was probably screaming in my head at the TV: “It’s not just a purse, it’s a Birkin bag.” Sheesh, even Emily Gilmore never got a Birkin bag from Richard! (And Samantha tried to get hers on “Sex and the City” five years earlier, but ultimately failed.) Knowing Rory, she probably used the posh designer “purse” to carry her books or something.

Sookie’s Elevated Chef’s Coats

Before Melissa McCarthy pooped in a fancy bridal shop sink and received an Oscar nomination, she stole our hearts as gourmet chef, half of Stars Hollow power couple (heeey, Jackson) and accidental marijuana farmer Sookie St. James. As Lorelai’s BFF and eventual Dragonfly Inn co-owner, Sookie spends a lot of time in the kitchen whipping up food critic-reviewed risotto, plus wedding cakes on the fly, thus requiring a closet full of elevated chef’s coats. She rocks a serious headscarf collection, too.

Sookie. Photo by Patrick Ecclesine/Warner Bros./Getty Images)

Sookie. Photo by Patrick Ecclesine/Warner Bros./Getty Images)

Everything Lane

Rory’s childhood best friend and indie rocking drummer was always a step ahead of the style game -- especially in small town-y Stars Hollow. (I mean, is there even a clothing store in Stars Hollow? Le Chat Club is the closest thing that comes to mind for fashion, but for just cats.) First, her stock of contraband club kid clothes, makeup and music (because we listened to physical CDs back then) that she conceals under her bedroom floorboards. That stash ends up being discovered by the terrifying Mrs. Kim that time she stays out past curfew for a disastrous CBGG gig; thus leading to a kicked-out Lane bunking with the rest of her Hep Alien band mates. Secondly, she had purple hair way before Nicole Richie and Ireland Baldwin -- if only for like two minutes, but a picture lasts forever. And, third, let’s talk about her wedding dress, which starts out as a frumpy monstrosity only to be customized into a convertible piece (long for the church part, mini for after-party) by couturier Lorelai Gilmore. But the ultimate trendsetter street cred: Lane dated Seth Cohen first. Only back then he was known as Dave Rygalski.

Lane rockin out. Photo by Patrick Ecclesine/Warner Bros./Getty Images

Lane rockin out. Photo by Patrick Ecclesine/Warner Bros./Getty Images

The New and Improved Jess

His clothes just say everything about him. When teenage heartthrob Jess Mariano reluctantly lands in Stars Hollow to stay with his Uncle Luke, he broods about (and breaks up Rory and Dean = Dory?) in his subversive moto-jackets and hoodies. Never mind his penchant for triple layering over long sleeve white t-shirts. Fast forward to Rory dropping out of Yale and socializing with the DAR crew and whiling away time with an oft-drunk BF Logan. The reformed heartbreaker pops up in an interesting role reversal -- Jess has written a novel and joined an indie publishing house in Philadelphia. Of course, along with his professional evolution from vest-wearing Wal-Mart employee to publishing magnate, his wardrobe game has elevated, too. Now Jess is smoldering in grown up selvedge double denim and responsible blazers (but over a graphic t-shirt of course. He is a hipster now.)

Rory and Jess. Photo: Patrick Ecclesine/Warner Bros./Getty Images

Rory and Jess. Photo: Patrick Ecclesine/Warner Bros./Getty Images

Lorelai’s Tear-Inducing Orange Sweater

Yes, the final season of “Gilmore Girls” was uneven, to say the least, largely due to the departure of show runner Amy Sherman-Palladino. But us die-hards were way too invested to not see how Lorelai, Rory and the rest of Stars Hollow would sign off. (I’m tearing up as I write this.) Rory scores a then-groundbreaking gig as an online(!!) political reporter covering the Obama campaign trail and has to peace out ASAP. Lorelei helps her daughter pack -- and inadvertently gives us some travel tips -- by ironing every single piece of clothing (“the flatter the clothes, the more will fit in your suitcase”). She also crams in as much last minute advice as possible in that signature Gilmore fast-talking, extended monologue type of way and decides to part with her coveted (unseen) orange sweater.

“I know you’ve wanted it and now I’m—you know what—finally gonna give it to you,” she says to her daughter. Then Rory responds, “Mom… You’ve given me everything I need.”

And then it was ALL worth it. Cue the tears, no SOBS. Lots of them.

So there you go. If a bajillion critical reviews and legions of obsessive fans aren’t enough to convince you to watch (or re-watch) Gilmore Girls on Netflix come October 1, maybe the FASHION will. And don’t forget to have lots of tissues on hand, plus some really good eye cream for the aftermath.