Gilmore Girls Is One Of The Most Iconic Shows, So Here’s How To Dress Like Them

Ah, the early 2000s – when jeans were all low-rise, bandanas were a key accessory, and denim on denim reigned over us all. Yes, the fashion in the 2000s left much to be desired, but at least the TV shows will never go out of style. 

While many people were settling in to watch their first glimpse of Grey’s Anatomy, finishing up Sex and the City, or even enjoying the last stylish years of Friends, I was taking scenic walks through Stars Hollow. 

There are very few TV shows that completely embody the feeling of coming home, to me, but Gilmore Girls is one of them. I watched it when I first moved away from home, every time I’ve had my heart broken, and of course, every autumn because you can’t have leaves falling and not watch Gilmore Girls. It’s a sin. 

If you haven’t seen the show, please watch it. I suggest it to anyone who needs a mother, friend, imaginary boyfriend (or three), and a general mood booster.  

The Gilmores were my family for years. I’ve watched the entire show at least seven times, all the way through, not to mention my favorite episodes, which I rewatch far too often. I fell in love with the characters and soon began to take on their traits. I talk fast because of Lorelai, read all the time because of Rory, and make my opinions heard because of Emily. 

This week, I was able to live out my lifelong dream of being a Gilmore girl by recreating some of the show’s iconic (if not somewhat dated) outfits. Life’s short, so talk fast, dress well, and be a Gilmore.

I thought this week would be much easier than it was. After all, I’ve seen every episode so many times and I know the characters – surely, I can dress like them. But after exploring their fashion, I realized I was going to have to take their 2000s style and make it my own. 

So please enjoy this updated take on all the best Gilmore Girls outfits!

Lorelai Gilmore

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lorelai outfits

I had to start the week off with Lorelai! While she might get on people’s nerves, she’s definitely my favorite character. Lorelai’s style consists of two opposing wardrobes. On one hand, she’s a professional business owner who dresses to the nines and would never repeat an outfit (seriously, how much money did they have?). On the other hand, you have the music-loving, free spirit, bandana-wearing woman who doesn’t care what people think of her. 

While I could have chosen any of these, I chose to wear her iconic look from the revival. It’s pretty simple and comfortable, just like she likes it — a quarter-length gray and white striped shirt and overalls. Nothing too fancy. But this is one of my favorite scenes from the revival, so I had to add in the outfit.


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Gilmore girls outfits

I spent the entire day out before I realized my outfit was slightly inspired by Sookie! I had been worried that I wouldn’t get the iconic baker into my challenge, as I don’t have chef’s tops and I don’t wear bright colors too often. I think Sookie St. James would approve of this outfit. 

I stuck with the young look that she often maintains, always wearing lighter colors, bright bandanas, and curly pigtails, but then I updated the look a bit. I decided on a more neutral tone with my khaki jumpsuit, all while keeping with her original spirit.

Luke’s ‘Uniform’

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Gilmore girls outfits

I knew Luke’s outfit would be my favorite. I always try to incorporate a pajama or casual look into these challenges because I work from home and don’t see the point in getting dressed every day. 

I grabbed one of my oversized flannels, my baggy mom jeans, and a blue baseball cap and was done! I can understand why Luke wore this every day – this was by far the most comfortable outfit of the week.

Rory’s Uniform

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Rory Gilmore

I couldn’t do a Gilmore Girls article without talking about the uniform! While I love the idea of uniforms, I know that they’re not high fashion. I took elements of her uniform – namely, the iconic skirt and jacket – and made them into another outfit, one that you can wear out without people assuming you’re in high school. 

Emily’s Pants

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Gilmore girls outfits

I ended on a strong note or maybe a strong character. Possibly both. I love Emily Gilmore. Her quips, her style, and her obstinance keeps the show more relatable than anything else, in my opinion. Emily always looks so stylish in her suits and dresses. While I’d love to say I wear outfits like that all day, I don’t. 

I grabbed some of my favorite cigarette pants and a black t-shirt. I cannot imagine Emily Gilmore wearing a t-shirt, but I updated the looks. I think I got her style down, and I loved feeling a bit more elevated than I usually do.

My Review

This week was a little more difficult than I thought. Also, the show was more dated than I remember. As always, it was a great way to get out of my comfort zone and try on outfits that I wouldn’t have, originally.

I think, from now on, I’ll just watch the show instead of dress like it.


Do you love Gilmore Girls? What challenge should I do next? Comment below!

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