Bootcuts And Bucket Hats: Already-Dated Fashion Of Gilmore Girls

Just about every week in the early 2000s, I’d catch the latest episode of Gilmore Girls on the WB and swoon over the latest fashions. When I rewatched the series this year, I found myself cringing instead – over my own sartorial past. It’s not that the clothes in Gilmore Girls were exceptionally bad. Actually, a surprising number of looks hold up, a real testament to the costume department. It’s just that the show aired a long time ago. Let’s put it this way. When Gilmore Girls premiered, we were one year younger than Rory. Now we’re, like, a few years younger than Season One Lorelai.  We’ve already written a post on Mid-2000s fashion, but now let’s take a look at how those trends played out in Stars Hollow.


Message Tees

Whether it was a sassy slogan a la Seth Cohen, or a bowling alley that you’ve never been to because it doesn’t exist, we were all about the message tees back at the turn of the millennium. It seemed like a way to let people know something about you without even having to say a word — but from the shores of 2015, I wonder why I really cared that people knew that I found reading sexy. Even if it is.

Really proud I never rocked one of these. See also: Jesus Is My Homeboy.

The tiny blazer – bootcut – t-shirt trifecta

I wore this look a lot in college (2004 – 2008), and so did Rory. You felt a little more put-together than if you were just wearing a t-shirt. What Not To Wear was big at the time, and I think we all thought that this was supposed to “balance our proportions” – but it kind of did! Bonus points if you remember why Rory’s not wearing a shoe in this scene.

Skinny Scarfs

You live in Connecticut. Connecticut is cold. Why so little scarf? We all had these and we all looked like we were wearing evidence of a knitting accident.

Bucket Hats

A couple years ago I joked that I’d know people were taking the ’90s revival too far when bucket hats came back. That’s because I couldn’t fathom a world in which bucket hats came back. That’s because I’m an idiot. And in the late 90s and early 2000s, we were all idiots, wearing headgear like a sassy fishmonger.

By the way, the bucket hat did come back, and I feel the urge to whisper “you’ll have regrets” whenever I see a teen in one. But whatever, I’ll let them have their youth.

“Bowling” shoes or whatever

Not a great picture. But remember in 2003 or so, when we realized that you could replace those giant puffy sneakers with a sleeker… bowling shoe, basically?

Lane’s “punk” look

We hit on this in the playlist post, too. The modern hipster look didn’t get big until around 2008, and before that if you wanted to show people you were a little different you’d opt for this Avril Lavigne-y, pop-punk aesthetic. Lots of hot pink, stars, and items that could be purchased at Hot Topic.

Full, knee-length skirt + long, fitted top + cropped sweater

That sounds like a really specific look, but it was widespread and was absolutely, 100% my jam circa 2005. I wouldn’t call this “dated” it just isn’t as big as it was for a while there. Full disclosure: I think this might be a dress, but I couldn’t find the outfit I was remembering.

Short sleeve shirts over long sleeved shirts

If you needed a little extra warmth – but not like, sweater-level warmth – and you wanted to be cool, and it was 2004, you’d do this. People have always layered t-shirts under other clothing, but in the early 2000s we decided to really let those gray Hanes t-shirts shine.

Two-colored tie dye shirts 

Granted, it was laundry day. But remember these two-tone tye-die numbers that always made you look like a pert camp counselor? This is pretty inoffensive as far as “ran out of clothes” clothes go, but I haven’t seen one of these little numbers for years. Granted, I haven’t been hanging around any summer camps, either.

That one kind of leather jacket that ladies used to wear

No, but you know what I mean. It’s not as though leather jackets, as a category, will ever go away, but that one kind of leather jacket was all over the place way back when. I remember going with my friend to Wilson’s – remember Wilson’s? – so she could buy one. I blame Lorelai Gilmore and Buffy Summers. The WB in general, really – may it rest in peace.

 I think we told ourselves this was “harajuku” inspired

Let’s be real, Japan never asked us to do this. There’s just so much mixing of patterns and collars. I don’t think you understand. You could buy these at stores 15 years ago.

Triangle hair bandanas

Something weird happened with these. Triangle bandanas were super popular in the early 2000s, and you could even buy them pre-cut into a triangle shape with strings in the back. We thought it was sporty and cute. To wear rags. On our heads. Like washerwomen. I wore one, even though it made me look like my Irish peasant ancestors even more than usual. Then, after they faded with fashion, they held on for a few years — but only with super Christian girls. Girls who got those special Christian teen magazines and listened to Newsboys? LOVED these triangle hair bandannas.

Jean Skirts + wacky tights + blazer + scarf

I’m no mathematician, but I’m pretty sure that was the formula for fashion success around 2007.

Peasant Dress + Boots

Peasant skirt + boots was also an acceptable combo. Lindsay Lohan and Sookie St. James were in accord on that one.

“Going out” tops

In our Mid-2000s Fashion post we discussed going out tops, and Lorelai owned many. These were lacey, satin-y, or otherwise frilly tops you’d pair with your boot-cuts to transition easily from dinner at your parents’ to some sort of club.

Is it a slip? Is it a dress? Neither. It’s a mistake.

In the late ’90s and early 2000s – maybe as a reaction to the over-the-top foof of the ’80s and early ’90s – we all loved the simplicity of a slip dress. But slips belong under a dress for a reason. For the record, a lot of the “going out tops” of the day also looked like fancy lingerie. You might be fooled because Alexis Bledel and Lauren Graham both look nice here – but on common folk, close-fitting, clingy satin is a surefire way to look like you’re made of weird flesh lumps.

Christmas sweaters

Okay, it was just that one time.