Warner Bros.
Sundi Rose
January 03, 2018 4:33 pm

The original Gilmore Girls series began airing way back in 2000 (when I was still recording the episodes on a VCR) and even back in the early 2000s,  Lorelai was always the QUEEN of fashion. Whether it was a skinny scarf or a too-shiny button-up, Lorelai understood a good ’00s outfit. Now that it’s 18 years later, some of her best outfits don’t really hold up—but we decided it was worth a look back. We hope you’re inspired to bust out your best bootcut jeans and bandana. Here’s some the best (and worst) of Lorelai’s most ’00s fashion.

That shrunken sweater, though

We not sure who decided it was a good idea to only make a sweater that covered your shoulders, but Lorelai had to have something to cover all those cute wrap dresses.

Perky pigtails

Behind-behind-the-ear pigtails were all the rage for women in the early aughts. It showed you were fun and low-maintenance. Sounds like our Lorelai, right?

The higher and spikier the hair, the better

Any ’00s lady worth her weight in Frizz-ease knows that you gotta get that bun high and you gotta get those chunky pieces as spiky as possible. Lorelai’s eye-gouging hair struggle was real, but it was a chance she had to take to get that hair as sharp as possible.

Teeny tiny skirt suits

Lorelai definitely learned from the Ally McBeal School of Professional Dress. The skirt had to be short, the shoes chunky, and that jacket better be cut tight at the waist.

Matted fake fur was a real thing

I guess we should be glad it wasn’t matted real fur, but looking back on this mess makes my 2018 eyes hurt. Leave it to Lorelei to look good with a used bathmat draped around her shoulders.

Everything about this

Those red sneakers, that cross-body bag, the silly graphic tee and oversized watch. Man, Lorelai was really getting more bang for her ’00s buck.

Oy with the bandana, already

Somewhere, in those early days, somebody decided that it was all the rage to walk around looking like Alice, The Brady Bunch maid, on her off day. It wasn’t. Couple that accessory with the lace-up baseball tee and Lorelai is forcing my eyes to just look way. Just look away, for heaven’s sake.

Never too much plaid

Okay, so a plaid overcoat might be a bit much. But, in Lorelai’s defense that useless, skinny little scarf is really breaking the pattern up for her.

Sheer always means formal

This classy little number had a lot going for it. Not only did it have the requisite shine all dressier dresses had, it also had spaghetti straps and a sheer bottom half. All the bases are covered here, right?

To brooch or not to brooch

Although that wrap dress is practically everything, and I would wear it right now, I have to question the ’00s tendency to ruin a good thing with loud jewelry. Besides being super distracting and silver, it also seems kinda like you’d be tugging your hair out of it all day.

Pretty, shiny things

After she out grew those tiny little suit-skirts, Lorelai’s professional dress went the way of shiny. This isn’t the worst of what we’ve seen (nor the best), but she better hope she stays calm and collected. Everybody knows that a satin shirt does not forgive sweat stains.

Sweater vests aren’t just for golf anymore

Of all the things I wore in those early days of the new millennium, I miss this sweater vest/button up combo the most. You had double the opportunity to show how put together you were, and if you were really cheeky, like Lorelai, you’d pair unexpected colors and patterns.

The ruffled tuxedo shirt: business on the bottom, party on the top

When the shiny shirts were in the cleaners (from all the sweat stains, obviously) and you were feeling more festive than a sweater vest would allow, the ruffled tuxedo shirt was the office go-to. Never let it be said that Lorelai Gilmore couldn’t appreciate a shirt that performed as work attire and a fun reminder of what happens when you get off (you know, because of the ruffles).

Clothes that don’t know what season it is

Because nothing says weather-confusion like a sleeveless turtleneck. I owned three of these and they were all cable-knit and went really well with all the long column skirts and chunky stacked wedges I owned — inspired completely by Loreali Gilmore.

Sports wear without a hint of sportiness

These striped hoodies and their accompanying pants were the yoga pants of the early aughts. They were extremely good for making it seem like you were much more athletic than you actually were. We all know Lorelai wasn’t much interested in anything that meant physical work.

Argyle is the new black

Not only did Lorelai double down on the sweater vest/button up combo, she really leaned into the argyle. We can’t really judge too harshly, though. Don’t forget the chevron craze that took over our closets not so long ago.

So much pleather 

Leather never goes out of style, but what makes this ensemble so particularly ’00s-ish, is its distinctive blazer-ish cut. A staple for the “working professional who wants to maintain their edge” Lorelai rocked this blazer over the course of several seasons — although it’s shape may have changed a little over the years.

It’s not her toddler’s shirt

Ah… the baby tee. Smaller seemed to be better during this era. Phones and computers were shrinking, and apparently, so were our clothes. Notoriously ill-fitting, Lorelai wore her fair share of shrunken t-shirts, usually with some sort of random graphic with little to no relevance to her life.

The empire waist v-neck

Universally flattering, the V-neck empire shirt looked good on every body type. Because this shirt was simply everywhere during the years between 2002 and 2007, it’s completely impossible to wear it without feeling transported to the early ’00s.

Before there were beanies… There was *this* thing.

Before the slouchy beanie, Lorelai was wearing this ridiculously cute combo: tight toboggan hat and skinny scarf. Always one to know how to rock those cold-weather clothes, Lorelai knew how to take the era’s most useless accessory (the skinny scarf) and make it work for her -even though it probably wasn’t working to keep her neck and chest warm.

The multi-functioning shirt

Not only does this work as a cute and on-trend blouse, this shirt also has a built-in necklace. This is super handy for ladies like Lorelai, who are just too busy, some days, to make decisions about their blouse and their accessories.

Now, take thee to the mall, because we’re itching for a teensy graphic tee.

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