Lorelai Gilmore is considered by many to be the greatest mom on TV. While she’s more famous for her coffee obsession than for her fashion sense, she definitely wears some interesting outfits over the seven seasons of Gilmore Girls (plus the four episodes of the Netflix revival).
Whether she’s walking to Luke’s Diner to get a burger or strolling around Stars Hollow with Rory, Lorelai usually looks great… except for the times that she doesn’t. Like the rest of us, Lorelai has some fashion mishaps, and she makes some style choices that leave us pretty confused. Here are Lorelai Gilmore’s five best and five worst outfits.
10. Best: Lorelai’s Pink Coats
Lorelai wears some great coats on Gilmore Girls, and she seems to have a thing for pink outerwear. She even wears this item of clothing in the Netflix revival.
Whether smelling snow in the Stars Hollow air with Rory by her side (and trusty cups of coffee in hand) or talking on the phone, the TV mom looks awesome in this color. She proves that it’s always a good idea to pick a bold color.
9. Worst: This Awkward Red Dress
Part of the deal that Lorelai makes with her mom, Emily, so that Rory can attend the super fancy high school Chilton is that they’ll come over for dinner on Friday nights. This isn’t just any family dinner, though. This is Friday Night Dinner where you’re supposed to dress up, you have drinks in the living room, and one of the many staff members that Emily has hired announces that it’s time to sit at the table.
While Lorelai wears a variety of nice, elegant dresses over the years, this red dress is pretty awkward. It’s definitely one of her worst looks ever since red isn’t her best color and the huge black plastic belt is too distracting.
8. Best: This Leather Jacket And Skirt Combo Giving Fall Vibes
Fall is the best season, and fall on Gilmore Girls is especially wonderful. It’s so much fun to watch Lorelai and Rory walk through their small town, wearing cozy coats and scarves with colorful leaves all around them. Stars Hollow is also famous for its festivals, like the Autumn festival in the first season episode, “Kiss and Tell.”
The outfit that Lorelai is wearing here is so great, and it’s one of her best outfits for sure. Her long leather jacket, dark brown sweater, and light brown skirt give us all the fall vibes that we could ever want.
7. Worst: Anytime She Wore A Bandana
The truth is that no one should ever wear a bandana. That just seems like a fact of life, right?
Unfortunately, Lorelai Gilmore seems to really enjoy wearing bandanas…. at least according to the number of times that she’s worn one on Gilmore Girls. In the photo on the left, she’s got a bright green one on, and in the photo on the right, she’s chosen a red one. Neither bandana matches her shirt, either, so both outfits are awkward and weird.
6. Best: Her Plaid Shirt And Vest
There’s something really warm and cozy about Lorelai’s outfit in this episode. She wears this red plaid shirt, brown hat, brown vest, and jeans in the Netflix revival A Year In The Life. In the “Fall” episode, Lorelai leaves Luke and Stars Hollow behind to go on a hike. She’s inspired by the famous and popular book and movie Wild.
Of course, this is Lorelai, so she doesn’t actually go hiking. But she has good intentions, and she needs to clear her head after all of the personal drama she’s gone through with Luke. This image of Lorelai crying on her cell phone with the beautiful wilderness behind her is pretty perfect.
5. Worst: The Rhinestone Sweatshirt And Leopard Cowboy Hat
The rhinestone sweatshirt that Lorelai is wearing here comes with a pretty dramatic story: it once belonged to Rachel, who was Luke’s one true love (well, his one true love before Lorelai moved to town and stole his heart). Rachel is a free-spirited photographer who can’t stay in one place for very long, and watching Lorelai wear the item of clothing is way too much for Luke’s sensitive soul.
It’s also too much for us. This sweatshirt is bad enough but pairing it with a cowboy hat that is also leopard print? This is one of Lorelai’s worst outfits.
4. Best: Lorelai’s Cozy Red Coat
Again, Lorelai Gilmore does wear a lot of coats on this TV show, and she looks amazing in so many of them.
This red coat is so cozy-looking and immediately gets us excited for winter and all of its warm vibes, so we’re going to say that it’s one of the best outfits that she wears on Gilmore Girls. This style of coat with the shearling on the inside is coming back in style so even though this show was on the air in the 2000s, this is still a great fashion statement to make.
3. Worst: This Weird Umbrella Look
The “Summer” episode of the Netflix revival isn’t one of the better outings, and the scene where mother and daughter head to the pool is particularly weird. It’s really confusing that Lorelai and Rory are holding umbrellas in this photo. Yes, it’s sunny, but they look silly and ridiculous.
Besides the fact that Lorelai is holding an umbrella, she’s wearing a dress (or cover-up, it’s hard to tell what it is) that has a super loud pattern on it. It’s just not something that we want to see this character wear.
2. Best: When She Paired A T-Shirt With A Jacket
Another one of Lorelai’s best outfits is when she pairs a t-shirt with a graphic print on it with a leather jacket. For one thing, Lorelai looks awesome in leather jackets. She’s the coolest mom ever (yes, perhaps even cooler than Regina George’s mom in Mean Girls) and this is totally reflected in this choice of outerwear.
Sure, people could say that this character is simply wearing a t-shirt, jacket, and jeans, and sure, she is. But there’s something special about this combination. It’s a great casual outfit.
1. Worst: Lorelai’s Chilton Outfit
Finally, here’s Lorelai’s absolute worst outfit, and it’s one that every fan knows by heart: the outfit that she wears when it’s Rory’s first day at her new school.
Lorelai wears this super odd combo of clothing in the second episode of season one called “The Lorelais’ First Day At Chilton.” It’s not Lorelai’s fault, of course. She had a great suit ready… except she didn’t get it in time from the dry cleaners. Now Lorelai has to wear jean shorts and a pink tie-dye t-shirt. She tries to make things better by wearing a long coat, but since the headmaster makes her take it off, everyone sees what she’s wearing. Lorelai is the coolest mom and never embarrasses her daughter, but this was not only a fashion mistake but also a humiliating moment for both of them.
