The top 10 best outfits that Lorelai and Rory wore on Gilmore Girls

Oh, don’t mind us, we’re just rewatching Gilmore Girls for the millionth time…

The hit show – which ran from 2000 until 2007 – has captured our hearts in many ways, but one thing that we particularly adore about it is its exploration of fashion. 

Now, we admit, there are several outfits during Gilmore Girls’ seven seasons that we definitely would never wear today. Many of them are now seen as a fashion time capsule for the early 2000s. 

However, if you watch it often enough, you quickly realise that the show has quite a few stylish gems hidden in its wardrobe – particularly when it comes to the main characters of Lorelai and Rory Gilmore.

This mother-and-daughter duo were definitely ahead of their time in terms of fashion sense, and so we have picked out our top 10 favourite outfits from both women. Every time we embark on a rewatch, these outfits wow us:

Lorelai Gilmore

Season 1, Episode 7 – Kiss And Tell

As we all know, the gals of Gilmore Girls are the queens of autumn fashion, and Lorelai is no exception! This outfit is taken from one of the earliest episodes of the show, and yet it has aged like a fine wine. This brown turtleneck jumper and camel skirt is a timeless outfit. Pair it with a leather jacket and some knee-high boots, and you’re good to go.

Season 2, Episode 22 – I Can’t Get Started

Coincidentally, Lorelai and Rory end up matching in this stunning blue dress, as they take part in Sookie and Jackson’s wedding ceremony in the role of Sookie’s bridesmaids. However, we think that Lorelai really shines in this gown. It compliments her features beautifully, and although the episode doesn’t end happily for her (thanks to Christopher leaving her, again), she still glows in it!

Season 4, Episode 5 – The Fundamental Things Apply

This little number is definitely a fan favourite! Despite Lorelai struggling to keep up with the demanding renovations of the Dragonfly Inn, she still manages to retain her effortless sense of style. This red checkered sweater-vest is super chic, and we love the skirt and boots combo. Paired with actress Lauren Graham’s adorable curls throughout season 4, this outfit will always be a winner to us.

Season 4, Episode 21 – Last Week Fights, This Week Tights

This dress will always hold a special place in our hearts – not just because it is worn during the turning point for Luke and Lorelai’s romance, but also because it is just such a gorgeous dress! All dressed up for Liz and T.J’s Renaissance-themed wedding, Lorelai finishes off this look with an adorable flower crown in her hair. Luke really means it in this episode when he tells Lorelai she looks beautiful – as he should.

Season 5, Episode 13 – Wedding Bell Blues

This is Gilmore Girls’ 100th episode, and boy, does Lorelai pull out all the stops to celebrate it! Our favourite inn owner wows in this radiant, silver dress as she attends her parents’ vow renewal ceremony. She does pair the dress initially with a glitzy, pink cardigan, but personally, we think this gown works just fine on its own.

Rory Gilmore

Season 1, Episode 9 – Rory’s Dance

We see this dress as the very first outfit that Rory truly shines in, and it’s made even cuter by the fact that her mother Lorelai handmade it for her. Attending her first ever school dance with her boyfriend Dean, Rory looks positively adorable in her deep blue dress. We also love her hair’s up-do with its delicate flowers. Admittedly, we’re not a fan of the clunky boots that she pairs with this beautiful dress – but it was the 2000s, so we can forgive her for that.

Season 4, Episode 6 – An Affair To Remember

Yale Rory has some iconic fashion looks, and this is just one of our favourites! Not only did actress Alexis Bledel give herself a fresh start in season 4 by cutting her hair short, but she also gave Rory an upgraded sense of style. In particular, we love this look – the high-neck sweater looks incredibly cosy, and it goes super well with the brown plaid skirt. So chic!

Season 5, Episode 7 – You Jump, I Jump, Jack

Fans absolutely adore this incredible ball gown that Rory wears to the Life And Death Brigade celebration – and we can definitely understand why! The floral detailing on this dress is absolutely mesmerising, and it is such a flattering shape on Rory. The combination of her half-up-half-down hairdo finishes off the outfit with a timeless look.

Season 5, Episode 13 – Wedding Bell Blues

Just like Lorelai, Rory also ends up serving an iconic look in this episode! As her grandfather’s best man, Rory adorably decides to wear a suit to the vow renewal ceremony – and she ends up looking amazing, as always. We particularly love her hairstyle in this episode – the curly, low bun look suits Rory perfectly.

Season 6, Episode 7 – Twenty-One Is The Loneliest Number

Although we can’t bear to watch this era of Gilmore Girls due to Lorelai and Rory’s painful estrangement, we also can’t deny how much we love this dress! Rory wears this stunning gown to the party her grandparents throw for her 21st birthday. The black-leaf patterned dress gives Rory a sophisticated look, signalling the beginning of a new chapter for her. Plus, we have to admit that we do love the addition of her fringe in this season!