4 Rory Gilmore Outfits To Wear This Winter

A Breakdown Of Rory Gilmore's Outfits

As opposed to other installments of From Costume To Closet (which feature multiple characters), since we're only doing Rory Gilmore's outfits, let's take a look at her approach to different events:

Casual — Rory is the epitome of the girl next door, and all of her everyday outfits are both comfortable and cute. Even when she wears something like a tee shirt and jacket, choosing fitted pieces, different proportions, or accessories means she never looks frumpy.

Formal — Our leading lady is a big fan of A-line silhouettes and classic ensembles, as well as feminine details. Feel free to go wild with embroidery and beading. Rory does! Mixing up your colors and textures is another fun way to visual dimension.

School — You won't want to copy Rory's Chilton uniform piece for piece (it is a school uniform after all), but there's plenty of inspo to draw from it. The entire uniform stays in the same navy, light blue, and white color palette, and she has some fun with accessories like a tie or headband. I'm also a huge fan of the way her yellow backpack provides some intense color contrast!

*The* Sweater

Sweater; Jeans; Necklaces; Ballet flats; Bag; Claw clip

This outfit has been absolutely immortalized in the pop culture zeitgeist, and honestly, for good reason. It proves you can be super comfortable without sacrificing style. (Plus the simplicity of the outfit really lets Rory's classic early '00s hair take center stage, as it should). Trust me, this white cable knit sweater has been the softest addition to my closet. I added a few recent trends to really bring this outfit into 2024 — delicate jewelry and ballet flats are huge right now, and tying everything together with shades of green means you have more freedom with textures and silhouettes.

The Chilton Uniform

Bodysuit; Coat; Jeans; Bag; Sneakers; Hair bow; Espresso martini

Because we don't want to walk around town in a fictional school uniform, I took a scaled-back approach to this Rory Gilmore outfit. I kept the same blue and white color palette thanks to this two-toned coat (and added some academic plaid with a hair bow), and adding details like flared denim and metallic sneakers elevates pieces that could look super basic otherwise. And in honor of Stars Hollow's most beloved drink, I found these super cute espresso martini earrings I'm *obsessed* with!

The Dance Dress

Jumpsuit; Heels; Hair pins; Clutch; Earrings

Holiday party season is quickly approaching and there are a few classic fabrics that wind up in my rotation: sequins, satin, and velvet. Instead of the traditional holiday dress approach, I switched it up with this velvet jumpsuit in a totally intoxicating blue. Strappy heels feel like a nice contrast to the full, lush look of the jumpsuit, and since I've always loved with the flowers in Rory's hair, I paid homage with a few pearly hair pins. If you'd rather go a more artsy, modern route, add these sculptural earrings instead of the pins.

The Stars Hollow Gazette Look

Dress; Coat; Boots; Scarf; Earrings; Bag

A dress + coat + shoulder bag combo will literally never go out of style if you ask me. I turned this look into something more monochromatic, but since the dress and coat are different tones, there's a little bit of dimension. Even though the suede boots have a similar finish to the sweater dress, the stiletto heel adds some edge that you'd also get from a leather block-heel boot! Finally, for some extra color (and in honor of the one and only Lorelai), add a multicolored scarf and pink bag. Since they both feature some gray tones (instead of bright neons), they don't overwhelm the outfit at all — in fact, they'd look just as good with the white sweater outfit as they do with this!