I Dressed Like Lorelai Gilmore For A Week & Here's What Happened

If you've seen even a single episode of Gilmore Girls, you probably know that it involves lots of coffee, the best mother-daughter relationship in TV history, and Milo Ventimiglia being dreamy AF. But if you're a true fan of the show, you also know that throughout its seven-year run, Lorelai Gilmore wore some wonderfully crazy sh*t. From her "Look at me, I'm adorably kooky!" style in Season 1 to the endless array of Diane von Furstenberg wrap dresses she could inexplicably afford near the end of the series, Lorelai Gilmore's fashion was one of my favorite things about the show.

While I love her outfits, my own style is more Luke-Danes-with-midi-rings than Lorelai. That said, I'm one of the biggest Gilmore Girls fans out there, so when I saw other Bustle writers channeling iconic TV fashion, I decided that Lorelai's quirky outfits deserved an experiment of their own. Inspired by news of the Gilmore Girls Netflix revival and my obsession with the original series, I decided to dress like Lorelai Gilmore for a week. Emily Gilmore would not have been pleased.

The Experiment

With seven of Lorelai's most iconic looks in mind, I did one thing Emily Gilmore would be proud of: I headed to Bloomingdale's to gather some of her wardrobe staples. Since I live in Manhattan in 2016 and not in Stars Hollow in 2000, I also relied on Modcloth, ASOS, and my co-workers' closets to compile all of the necessary clothing and accessories. Then, one Monday morning in the middle of winter, I put on some cutoff shorts and started my week-long, caffeine-fueled fashion journey.

Day 1: Rory's First Day At Chilton / My First Day Getting Absurd Looks From Strangers

I decided that it was best to start my fashion experiment by diving right in with her most batsh*t crazy look of all time. If Lorelai could wear cutoffs, cowboy boots, a tie-dye tee, and a long black jacket on Rory's first day at Chilton, then I could try the outfit on my first day as her.

Duster Coat, $73, Asos

Fashionista called this outfit "street style bait these days for sure," so I was half-expecting to be stopped by a photographer on my way to work. That didn't happen, but I did get an odd look from an older woman who was waiting for the bus!

The main thing that struck me about Lorelai's laundry day getup was the sheer ... floppiness of the jacket. I've been known to wear a pair of cutoffs and a tie-dye tee or two, but the jacket was by far the biggest departure from my typical style. I did appreciate that its length helped keep my legs from freezing off.

It's worth noting that in an office full of huge Gilmore fans, no one identified my look until halfway through the day. The editor who sits directly across from me commented that she liked my shirt, but it wasn't until about noon that she finally noticed that I was wearing shorts. In February. In New York. Another Bustler told me that I looked like I was ready for Coachella, while a third, extremely generous co-worker noted that she loved "how brave" I was to be wearing shorts in the middle of winter: "You look like you don't give a sh*t what people think." With that, I figured I could mark Day One off as a success.

Day 2: My First And Last Time Wearing A Bucket Hat

Bucket Hat In Black, $18, Asos
 My Flair Share Dress, $60, Modcloth

For my second outfit, I chose one of Lauren Graham's least favorite Lorelai looks: a paisley dress and bucket hat. Seriously, what's not to hate here? For reference, here's how Graham feels about the outfit today:

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Aaaand here's how my coworkers, now mostly in-the-know about my experiment, reacted upon seeing my bucket hat:

Co-worker #1: *bursts into intense laughter immediately upon seeing me*

Co-worker #2: "I hate these Lorelai outfits. I really like you, but I really don't like seeing you in these clothes."

Co-worker #3: "I think you look quite nice!"

Co-worker #1: *still laughing*

As for myself, I felt like I would have loved the dress back in 2002, but I can't recall ever having been a huge fan of bucket hats. I suffered through the hat for most of the day, but by 5 p.m. the floppy brim really got to me, and I had to take it off. In retrospect, looking at the photo above, I feel like that was probably a wise decision.

Day 3: The Bandana And Shirt From 2002

On the third day, it was cold and rainy outside, so I opted for Lorelai's "Season 1 / Season 2 sassy bandana look," since it didn't include some kind of skirt or dress. Spoiler alert: Lorelai's face in the GIF above = pretty much my thoughts about this outfit by the end of the day.

Hearts Print Bandana Neckerchief, $7, Asos

Here were some of the other reactions:

Co-worker 1: "HOW MANY MORE OF THESE OUTFITS DO YOU HAVE?! WHEN WILL IT END?!"

Co-worker 2: "Feel free to include in your article that it totally brightens my day each time I see you!"

Co-worker 3, after sitting in a meeting with me for about 40 minutes, finally gesturing to my bandana and pigtails: "Wait, what is going on here?"

While I have to admit that this wasn't my favorite Lorelai fashion moment, my doorman did greet me with a peace sign upon seeing my bandana when I returned home at night. Just another day in the life of Lorelai Gilmore.

Day 4: The Dance-A-Thon Look

Since the weather was finally warmer, I decided that day four would be Dance-a-Thon dress day. I knew I wanted to try Lorelai's sweetheart dress and curls at some point during the week, because while it's not her typical style, it's probably her best fashion moment from the entire series. I curled my hair, slipped on a Modcloth dress, and donned red lipstick for the first time since I attended a wedding six months previous.

All Manners of Merriment Dress, $80, Modcloth

Here's how people responded:

Co-worker #1: "You tried so hard today!" (Maybe not a compliment? But it's true. I did spend a lot more time getting ready than I usually would!)

Coworker #2: "You look so pretty today. I love your lip color!"

Co-worker #1 again: "You look like Hayley from the '90s!" (Again, not sure it's a compliment, but I like the '90s, so ... great?)

Co-worker #1, who really wouldn't stop commenting on my outfit: "You look like Hayley from the junior prom!" (True. And also something I'd take as a compliment.)

Co-worker #3: "Is this the Dance-a-Thon dress?" (Why, yes. Yes it is!)

I was sort of shocked to discover that I really liked the way the dress fit me. I felt like this was something I'd definitely wear again, sans vintage hair and makeup. When I typically buy dresses, I go for shapeless black shifts, but the sweetheart neckline had really grown on me by the end of the day. It was also suuuuuper comfortable.

Day 5: The Mother-Daughter Fashion Show Blazers

Since Emily is my favorite of all the Gilmore Girls, I had to include the mother-daughter fashion show ensembles in my experiment. I felt pretty strange going to work in a suit, since I'm usually wearing flannel and jeans, but any time I can dress like I work in the Ally McBeal office, I'm game. I also got to force my co-worker to act like Emily Gilmore.

Lafayette 148 Bonnie Topper $498, Bloomingdales
BOSS Victana Pencil Skirt, $265, Bloomingdales

Here's what other people thought of the red suits:

Co-worker #1: "Hayley, I CANNOT."

Co-worker #2: *bursts into laughter*

Girl on elevator in my apartment, who I've only ever seen at the gym before: "Where do you WORK?"

Day 6: Lorelai's Season 6 And 7 DVF Wrap Dresses

Since Lorelai's entire wardrobe in Seasons 6 and 7 basically consisted of one DVF wrap dress after another, I knew that if I was going to pay tribute to her full range of fashion, I needed to wear at least one wrap dress during this week. Seriously, look at all these!

Lorelai f*cking LOVED wrap dresses:

Seedbead Charm Long Necklace, $4, Asos 
DVF Studio LLC New Julian Two Dress, $398, B
loomingdales

I opted for a blue DVF wrap dress with long sleeves, since it was still somewhat cold in New York. It was honestly one of my favorite things I wore all week. And yes, I'm aware that my wrap dress doesn't look exactly like the one in the photo, but if you are a true Gilmore fan, you know that Lorelai would totally have worn my DVF dress, too. I donned the dress on a dinner date, and after rocking cutoffs, tie dye, and bandanas all week, a wrap dress felt very grown-up. Diane von Furstenberg dresses haven't changed much since Gilmore Girls aired, so this felt like the most modern look of the week. My doorman didn't even give me a weird look when I made my boyfriend take this photo in the lobby of my apartment building!

Day 7: Please Luke, Please Please Please (Let This Experiment Be Over)

To round out my week as Lorelai Gilmore, I recreated the first outfit we ever see her wear in the entire series. Her knit hat and pink cardigan aren't my style at all, but the finished look was pretty comfortable for brunch with friends.

Charter School Cardigan in Rose, $40, Modcloth

My friends' thoughts on the look:

Friend #1, graciously trying to compliment my very strange outfit: "I love that color blocking! Those are the Pantone colors of the year, right?"

Friend #2: "What ... is going on?"

Stranger in the restaurant: *dirty look of disgust* (I can only assume that she was annoyed that I was wearing a knit hat on an unseasonably warm February day.)

Conclusions

I thought my week dressing like Lorelai would leave me wanting to take more risks with fashion and try new things, but in reality, it kind of had the exact opposite effect. Gauging people's reactions was fun at first, but thinking so much about others' thoughts on my appearance just became kind of exhausting by the end of the week. I typically only worry about my own opinion when choosing clothing, so waiting for people to comment on my appearance just felt like a total waste of energy.

At the end of the day, I would much rather dress how I want to dress, unapologetically and without regard for what others will think of the look. Besides drinking coffee and talking quickly, I feel like that's the most Lorelai thing I could do, anyway.

Want more fun fashion and beauty stories? Check out the videos below and subscribe to Bustle on YouTube!

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Photos: Kara McGrath (1); Bianca Consunji (4); Giphy (9); Rosanne Salvatore (1); Macey Hall (1); The WB (6)

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