If you've ever seen an episode of Gilmore Girls , you probably know that it involves lots of coffee, one of the best mother-daughter relationships in TV history, and Milo Ventimiglia being dreamy AF. But if you're a die-hard fan of the show, you also know that Lorelai Gilmore wore some pretty crazy outfits during the show's seven-year run. From her "Look at me, I'm so weird!" styles from season one to the countless Diane von Furstenberg wrap dresses she inexplicably afforded toward the end of the series , Lorelai Gilmore's fashion is one of my favorite things about this show.
While I love her outfit, my own style is more Luke-Danish with midi rings than Lorelai. That said, I'm one of Gilmore Girls' biggest fans, so when I saw other Hustle writers channeling iconic TV fashion, I thought Lorelai's wacky outfits were worth trying out for myself. Inspired by the news that Netflix is re-releasing Gilmore Girls and my obsession with the original series , I decided to dress up like Lorelai Gilmore for a week. Emily Gilmore won't be happy.
this experiment
With seven of Lorelai's most iconic looks in mind, I did something Emily Gilmore would be proud of: I headed to Bloomingdale's to round up a few from her closet A must-have item. Since I live in Manhattan in 2016 instead of Stars Hollow in 2000, I also rely on Modcloth, ASOS, and my coworkers' wardrobes to collect all the necessary clothing and accessories. Then, one Monday morning in the middle of winter, I threw on some cutoff shorts and embarked on a week-long, caffeinated fashion journey.
Day 1: Rory's first day at Chilton/My first day getting strange looks from strangers
I decided it would be best to start my fashion experiment with one of her craziest looks ever. If Lorelai can wear cutoff shorts, cowboy boots, a tie-dye T-shirt, and a long black jacket on Rory's first day at Chilton, then I can try that outfit on my first day as her, too.
Dust coat , $73, Asos
Fashionistas called this outfit "today's street style bait," so I was half expecting to be stopped by photographers on my way to work. That didn't happen, but I did get a weird look from an old woman waiting for the bus!
What struck me most about Lorelai's laundry day look was the sheer... fluffiness of that jacket. I've been known to wear a pair of shorts and a tie-dye tee or two, but this jacket is by far the biggest departure from my typical style. I do appreciate that the length helps keep my legs from freezing.
Remarkably, in an office full of die-hard Gilmore fans, no one recognized me until noon. The editor sitting across from me said she liked my shirt, but she didn’t notice I was wearing shorts until noon. In February. in New York. Another hustler told me I looked Coachella ready, while a third, very generous co-worker said she loved "how brave" I was for wearing shorts in the middle of winter: "You look It doesn’t seem like” Don’t care what others think. "That way, I think I can mark the first day as a success.
Day 2: I wore a bucket hat for the first and last time
Black bucket hat, $18, Asos My Flair Share dress, $60, Modcloth
For my second outfit, I chose one of Lauren Graham's least favorite Lorelei looks: a paisley dress and bucket hat. Seriously, what 's not to hate here? For reference, here's what Graham thought of today's outfit:
Ah, this is the reaction of my colleagues after seeing my bucket hat. Most of them now understand my experiment:
Coworker #1: *bursts into intense laughter as soon as he sees me*
Coworker #2: "I hate these Lorelai outfits. I really like you, but I really don't like seeing you in these."
Coworker #3: “I think you look great!”
Coworker #1: *still laughing*
As for myself, I think if it was 2002, I would have liked this dress, but I don't remember being a huge fan of bucket hats. I wore my hat most of the day, but by 5pm the floppy brim was really uncomfortable and I had to take it off. In retrospect, looking at the photo above, I think this was probably a wise decision.
Day Three: Bandanas and Shirts 2002
On day three, it was cold and rainy outside, so I chose Lorelai's "Season 1/2 Trendy Hijab Look" since it didn't include some kind of skirt or dress. Spoiler alert: Lorelai's face in the GIF above = pretty much what I thought about this outfit at the end of the day.
Heart print turban scarf, $7, A sos
Here are some other reactions:
Colleague 1: "How many more of these costumes do you have?! When will it end?!"
Colleague 2: “Feel free to note in your article that you brighten my day every time I see you!”
Coworker 3 and I had a meeting for about 40 minutes and ended up pointing at my headscarf and braids: “Wait, what’s going on?”
While I have to admit this wasn't my favorite Lorelei fashion moment, when I came home at night, my doorman did greet me with a peace sign after seeing my hijab. It's just another day in the life of Lorelai Gilmore.
Day 4: Dance Marathon Styling
Since the weather has finally warmed up, I decided that day four would be Marathon Dance Dress Up Day. I knew I wanted to try out Lorelai's sweetheart dress and curls at some point during the week, because while it's not her typical style, it might be her best fashion moment in the entire series. I curled my hair, put on a Modcloth dress, and put on red lipstick for the first time since my wedding six months ago.
All Manners of Merriment dress, $80, Modcloth
Here's how people reacted:
Coworker #1: "You worked so hard today!" (Maybe not a compliment? But it's true. I did spend more time preparing than usual!)
Coworker #2: "You look beautiful today. I love your lip color!"
Coworker #1 added: "You look like 90's Hailey!" (Again, not sure if this is a compliment, but I love the 90s, so... great?)
Coworker #1, who literally couldn't stop commenting on my outfit: "You look like Haley at the junior high prom!" (It was. And I took it as a compliment, too.)
Coworker #3: “Is this a marathon dance dress?” (Why, yes. Yes!)
I was kind of shocked to find that I really liked the way this dress fit. I think I would definitely wear this again without the retro hair and makeup. When I usually buy a dress, I go for a shapeless black shift dress, but at the end of the day, the sweetheart neckline really suits me. It's also very comfortable.
Day Five: Mother-Daughter Fashion Show Blazers
Since Emily is my favorite of all the Gilmore Girls, I had to incorporate a mother-daughter fashion show outfit into my experiment. Wearing a suit to work feels weird since I usually wear flannels and jeans, but as long as I can dress like I'm working in the Winnie the Pooh office, I'm happy with it. I also have to force my colleagues to act like Emily Gilmore.
Lafayette 148 Bonnie Topper $498, BBOSS Victana Pencil Skirt, $265, B loomingdales
Here's what others are saying about the red suit:
Coworker #1: “Haley, I can’t.”
Colleague #2: *suddenly laughs*
The girl in the elevator in my apartment who I'd only seen at the gym asked: "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 was basically made up of one DVF wrap dress after another, I knew that if I was going to pay homage to her full fashion wardrobe, I needed to wear at least one this week. A wrap skirt. Seriously, look at all of them!
Lorelai fucking loves wrap dresses:
Seedbead charm long necklace, $4, Asos DVF Studio LLC New Julian two-piece dress, $398, Bloomingdales
I chose a blue long-sleeved DVF wrap dress because the weather in New York is still a bit chilly. This is honestly one of my favorite things to wear all week. Yes, I know my wrap dress doesn't look exactly like the one in the photo, but if you're a big Gilmore fan, you know that Lorelai would totally wear my DVF dress, too. I wore this dress on a dinner date, and the wrap dress felt so grown-up after a week of rocking cuts, tie-dyes, and headscarves. Diane von Furstenberg's wardrobe hasn't changed much since Gilmore Girls aired, so this feels like the most modern look of the week. When I asked my boyfriend to take this photo in the lobby of my apartment building, my doorman didn't even look at me weird!
Day 7: Please Luke, please please please (let this experiment end)
To round out my week as Lorelai Gilmore, I recreated the first outfit she wears in the entire series. Her knit hat and pink cardigan are not my style at all, but the final look is perfect for brunch with friends.
Rose Charter School Cardigan, $40, Modcloth
What friends think about the appearance:
Friend #1, generously trying to compliment my very weird outfit: "I love that color blocking! Those are the Pantone colors for this year, right?"
Friend #2: “…what happened?”
Stranger in the restaurant: *disgusted dirty look* (I can only assume she was annoyed that I was wearing a knit hat on an unseasonably warm February day.)
in conclusion
I thought dressing like Lorelei this week would make me want to take more fashion risks and try new things, but actually, it had the exact opposite effect. It was fun at first to gauge people's reactions, but by the end of the week, thinking too much about what other people thought of my appearance became a bit exhausting. I usually only worry about my own opinion when it comes to choosing clothes, so waiting for people to comment on my appearance feels like a complete waste of energy.
At the end of the day, I'd rather wear what I want to wear, unapologetically, and not think about what others think of the look. Anyway, I felt like it was the most Lorelei thing I could do besides grab a coffee and a quick chat.
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Photos: Kara McGrath (1); Bianca Consunji (4); Jiffy (9); Roxanne Salvador (1); Massey Hall (1); World Bank (6)
