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Bandanas, Band Tees, & More Lorelai Gilmore Outfits I Tried This Week

Now that fall is here, all I want to do is lock myself in my apartment, light some candles, grab a cup of coffee and watch all seven seasons of Gilmore Girls. No one can convince me that the series isn’t the epitome of fall nostalgia. Gilmore Girls is one of my comfort shows and reminds me of my childhood, especially the close relationship I have with my mom. Of the many characters in Gilmore Girls, I must say, the true heroine of the show is Lorelai. Her fast-talking, coffee-obsessed persona, natural charisma, and, of course, the iconic Lorelai Gilmore outfits make her a fan favorite, but I especially love the way she never wavered from her authentic self. 

This fall, I’ve been seeing #LorelaiGilmoreCore all over social media, a trend in which content creators recreate Lorelai’s most iconic outfits from the show — from her signature boots and dark-washed boot cut jeans to turtle necks and band tees. As a diehard fan of Gilmore Girls and true Lorelai stan, I challenged myself to dress like Lorelai Gilmore for an entire week, and I documented my experience every step of the way. Here’s how it went.

Day 1: Pink Tie Dye, Denim Shorts, & Boots

I had to start off my week with —dare I say — the most iconic and hilarious look from Gilmore Girls. In season 1, episode 2, Rory starts her first day at Chilton Preparatory School. Lorelai is supposed to take Rory to school but wakes up late, which turns into a catastrophe when Lorelai realizes that all of her nice outfits are at the dry cleaners (it was “laundry day” in the Gilmore household). Lorelai ends up wearing jean shorts, a pink tie-dye shirt, cowboy boots, and a trench coat to cover her outfit, and although she did capture the eye of a divorced Chilton dad, the Headmaster and her mother were unimpressed by her antics. 

I don’t have cowboy boots, so to recreate Lorelai’s last-minute look, I opted for tall boots, my boyfriend’s pink tie-dye shirt, blue denim shorts, and a trench coat. When my boyfriend saw this getup, he asked if I actually planned on wearing it on the streets of New York. (Um…yes? If Lorelai can wear the outfit in public, so will I). Overall, I couldn’t help but laugh at this wonderfully random outfit and how it perfectly encapsulates the essence of Lorelai Gilmore. 

Day 2: Denim On Denim

If there’s anything I know about Lorelai Gilmore’s style, it’s that she’s not afraid to match denim with denim. Given that I frequently pair jeans with my denim jacket, this is a look I was confident in pulling off. When looking for inspiration, I came across a promo photo for the show where Lorelai is standing in the downtown area of Stars Hollow wearing low-rise denim jeans, a white tank top, a blue denim jean jacket, and brown square-toed boots. She’s pictured with her hands in her pockets and the classic Lorelai smize.

Unfortunately, I’m determined to leave low-rise jeans in the past — they’re just not my look, and I’m not even willing to thrift a pair. Sorry, Lorelai. Instead, to recreate this denim-on-denim look, I stuck to high-rise jeans, a white tank top, a denim jacket, and black Chelsea boots. It was an effortless look and I felt confident in it. Plus, there’s something about denim on denim during the fall that feels like a nostalgic throwback — I’m even starting to think Britney Spears and Justin Timberlake may have gotten their denim inspiration from Miss Lorelai.

Day 3: The Classic Turtleneck

I was particularly excited about my look on day three because it’s most similar to something I’d actually wear. The pink sleeveless turtleneck is the only article of clothing that I ended up buying before starting this seven-day challenge, and it was 100% worth it. Overall, it was a pretty simple look to pull off, and I felt happy and comfortable in it. Lorelai is great at picking colors that suit her, like the baby blue top here — and when I first tried on my own pink top, I felt like I was glowing, too.

Nowadays, my college routine can get mundane very quickly, but curating this outfit actually made me excited to get dressed and ready for the day. Day three reminded me that it’s important to wear colors and clothes that make you feel happy. Even on busy days when I have a packed schedule, it doesn’t take much time or effort to look good and feel good with a fresh outfit. 

Day 4: The “Friday Night Dinner” Outfit

Although Lorelai appears to be a single mom and manager of an inn on a tight budget, she sure knows how to break out the fancy dresses when she needs to (which I’m guessing is one trait she inherited from her mother, Emily). You’ll rarely see Lorelai re-wear one of her “Friday night dinner” looks, and her collection of fancy dresses hint at the fact that she has expensive taste. She is always dressed to the nines, especially for dinners at her parents’ house, and she seems to have an endless supply of slip dresses, skirts, and cute sweaters. 

For this look, I attempted to combine all of the elements of what Lorelai would usually wear for these weekly occasions. Sticking with the theme of finding the color that looks best on me, I wore a pink slip-style skirt, a tight high neck top, a little black sweater, and strappy heels. I was really looking forward to how these clothes would look and make me feel. Honestly, I wanted to look and feel effortless like Lorelai, but that was not exactly the case here — my sweatpants were calling my name immediately after I took these photos. Pro tip: Heels like these are not conducive for NYC streets. 

Day 5: When Lorelai Was A Painter For The Day

Lorelai loves wearing random hair accessories like bandanas and headbands, so I knew I had to plan a day where I did the same. Originally, I wanted to recreate a photo of Lorelai in a B-52’s band tee, but I couldn’t find mine, so I settled on a Black Sabbath band tee (which, to be honest, Lorelai probably wouldn’t wear — at least not unironically). I also took some creative liberty and grabbed a bedazzled jean jacket that was hand-painted by my aunt. While I don’t think Lorelai has a similar one, it seems like something Lorelai would absolutely adore. All of the random Lorelai elements of this outfit made me feel so happy and I could see myself rocking this outfit in NYC. It was a fun and comfortable outfit, which is all I could ask for in an outfit. 

Day 6: The “First Snow Day Of THe Season” Look

In the words of Lorelai Gilmore from season 1, episode 8: “It was the snow. You know how I get. It’s like catnip.” A true Gilmore Girls fan would know that Lorelai is obsessed with the first snow of the season because she believes it is good luck. It’s something she always looks forward to, and she literally has sensorial powers to predict the first snow — it is like a sixth sense that gives her snow forecasting instincts. As a born and raised Californian, I don’t know much about snow, but I do know that when I have witnessed snowfall, it is beautiful and peaceful — so I wanted to recreate this classic Lorelai look. I put on a blue scarf, blue beanie, a puffer jacket, jeans, and a pair of boots to complete the outfit.

The only downside of this outfit is that it wasn’t cold when I wore it, so I was overheating for the picture. However, I embraced Lorelai’s love of snow for a little bit and tried getting into the winter spirit while sweating a little in my puffer. Despite scraping by financially in the show, Lorelai always made the small things seem like the most special moments. Dressing up for this snow day look gave me joy, made me look forward to snow, and reminded me that the little things can really turn my day around.

Day 7: Just Another Day At The Office

If Lorelai and I have one thing in common, it’s that we’re both obsessed with coffee, and without it, we turn into miserable people (desperate times call for coffee via I.V.). In Gilmore Girls, whenever there is a scene at the Independence Inn, Lorelai can usually be found making a beeline to the kitchen in search of “coffee, coffee, coffee”. In honor of our mutual love for coffee, I decided to recreate this look from a scene in which Lorelai is demanding coffee from the kitchen of the Independence Inn before she starts her shift.  

Not to hate on Lorelai’s work outfits, but sometimes while watching the show, I would question how she got away with them. Granted, she looked fabulous, but she was often wearing short skirts and blouses with random designs — which is not exactly what I would choose for a long workday. However, after recreating this outfit from the iconic “coffee” scene, I almost felt too cute in the skirt and blouse. And even though I don’t think I’d consider actually wearing something like this to work, go off, Lorelai.

Honestly, I don’t think people give Lorelai Gilmore enough credit for how she owns her individuality. Although some viewers label her as annoying and childlike, in my opinion, she is always true to herself, never lets anyone get in the way of her dreams (or her child’s dreams!), and lets her unapologetic personality shine through her sense of style. This seven-day experience taught me that getting dressed for the day is more than just a necessary step of my morning routine; it’s a moment to remind myself that dressing in a way that makes me look and feel good leads to more self-love and body positivity.

Hi there! I am a senior at Marymount Manhattan College, double majoring in Digital Journalism and Politics & Human Rights. I am an Editorial Intern for Her Campus and I am the Editor-in-Chief of Her Campus MMM. Fun Facts: I love playing tennis and creating amateur TikToks in my free time.
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