Now That I’m in My 30s, I Just Want to Dress Like Lorelai Gilmore

Lorelai Gilmore is to a leather blazer as pumpkin spice is to a latte—you just don’t expect to have one without the other once autumn hits. And in my quest to find the perfect one, I came across this Quince number, which strikes all the right chords. It’s crafted from 100 percent leather, has a sleek and slender cut that’s more timeless than the oversized fits of today and, of course, has two patch pockets fit for a gal on the go. Now all it needs is…

…the perfect turtleneck to go under it. Slim-fitting and oh-so sophisticated, this ribbed sweater, also from Quince, is a dead ringer for the knit Lorelai wears in what I (and plenty others) would consider her best outfit of the series, paired with aforementioned leather blazer. This beauty has that perfect late ‘90s look, and is made from featherlight, 100 percent cashmere that was made for layering on a crisp day in Stars Hollow.

Lorelai’s love of suede and penchant for pencil skirts are both accounted for in this perfectly earthy (and a little bit flirty) pick. The soft, faux suede fabric signals comfort, as does the elasticated waist that’s hidden behind a smooth front panel. I can already tell that it’ll be a lifesaver on days I’m running late and have mere minutes to look put-together, and thanks to some well-placed darting, the stretchy, pull-on style is bound to look totally tailored—and way more expensive than its $25 price tag.

A pair of tall leather boots are a must for anyone hoping to follow in the elder Gilmore’s fashionable footsteps this fall, and this leather style certainly fits the bill. Between their rich brown hue, low block heel and widened almond toe design, these boots were made for walkin’—straight to Luke’s, for another coffee.

One of the Lorelai looks that lives rent-free in my head is a purple sweater dress with matching neck scarf that she dons early in the first season. While I've yet to sniff out the exact style, this cowl-neck top comes pretty close to achieving the same effortlessly elegant vibe courtesy of that skinny scarf detail. Bonus points for the flattering ruching that gives the figure-skimming viscose piece some texture.

Our girl has never met a pair of dark-wash bootcut jeans she didn’t like, and I imagine this mid-rise style would be no exception. They’re snug through the hips, thighs and backside, then widen into a subtle flare below the knee, making them great for donning with everything from leather booties to strappy sandals. And since they’re made with 99 percent cotton and just 1 percent elastane, holding their form (and, therefore, yours), should be no issue.  

When she’s not dressing up for a day running point at the inn, everyone’s favorite cool mom can be found in one of these whimsical, flowy, floral tops—a staple of the early ‘00s. So imagine my surprise when I spotted this lovely lace-trimmed blouse at Old Navy. A true blast from the past, it features delicate floral detailing and a camisole-inspired lace trim signature to Lorelai’s closet, plus an elastic seam at the back that ensures it shows off some of your shape.

From date nights with her circle of suitors to Friday night dinners with Emily and Richard, Lorelai never fails to clean up in slinky, whimsical frocks—much like this mesh-overlaid one from Maeve. The romantic puff sleeves and gathered bust feel direct from an early aughts romcom, while the shirring at the side creates a forgiving drape across the bodice. And don’t even get me started on the stunning floral pattern. For a prime Lorelai vibe, I’d layer it with an embellished cropped cardigan or lightweight shawl.

To mix up her managerial wardrobe without ever looking matronly, Lorelai reaches for silky button-downs emblazoned with bold prints. And, of course, blue is her color. So obviously I could see her (and me) in this satin top, boasting a slick sheen and striking splash of florals. Professional with some personality—we love to see it.

A more modern take on the shrunken styles Lorelai rocks to work on occasion, this polished piece is a perfect example of how to wear a vest in 2025. Everything from its double-breasted button front to its waist-cinching belt and sharp lapels makes it feel smart and elevated. And that luxe-looking heritage plaid? Even Emily Gilmore would approve.

Naturally, I couldn’t finish out this closet checklist without at least one animal print or wrap-style dress, and here we have a piece that combines the two in true Lorelai fashion. The funky zebra stripes let a little wild child energy shine through, while the button-front top and faux wrap skirt keep it classy. Plus, it’s made from a fluid-like crepe de chine that I can attest feels as light and airy as it sounds. I might not have any parent-teacher conferences to sprint to after work, but I’d definitely don this beauty to a weeknight cocktail sesh.