Books & Movies, Style

Timeless Style Inspiration from You’ve Got Mail

You’ve Got Mail is having a popularity resurgence lately, and I hate to be “that blogger” but it’s always been one of my favorite movies. (And, to be honest, most of my fall outfits have always closely resembled Kathleen Kelly’s truly perfect wardrobe. I’ve been wearing and writing about my love of turtlenecks forever. In fact, a post about the wonders of the turtleneck was one of the first pieces I wrote here!) There’s nothing like a good turtleneck, or twinset, or turtleneck/cardigan combination.

But Kathleen Kelly has always been one of my favorite characters for other reasons–because of her deep and unembarrassed love of literature; her earnestness; her goodness. The earnestness is especially poignant in this world today–the way that cynicism is the default option nowadays is disheartening and disappointing. I want to embrace Kathleen’s earnestness, her joy in small things–books, flowers, the fall weather.

Every year, I take an hour or so on a fall afternoon to walk through Manhattan, listening to “Dreams” and just soaking in the perfection of New York in the fall. It’s truly the season where the city shines the most. This movie, and that song, also remind me of living in the city with my husband and taking our walks through Central Park every day.

So, back to Kathleen’s style. You’ve Got Mail was released in 1998 but I would still wear–and do still wear–her outfits any day of the week. I’ve pulled together five staples that you’d find in Kathleen’s closet below. Let me know what you think!

A great turtleneck

A great turtleneck is the base of most of Kathleen’s outfits. Whether a turtleneck sweater (I love Everlane* and Bloomingdale‘s* cashmere) or just a cotton turtleneck*, alone or with a cardigan, a turtleneck is definitely Kathleen’s top wardrobe staple.


When did tights go out of style? I wear opaque tights all throughout the fall and winter and Wolford tights* last forever without getting worn out. They are expensive but well worth it!

A pencil skirt
A classic piece that’s gone in and out of popularity, a pencil skirt is still one of those perfect fall items. Pair with a turtleneck and tights for a simple, chic outfit that will work on anyone at any age. I’m on the hunt for a great camel pencil skirt for the fall.

A cashmere scarf
One of the most memorable scenes from You’ve Got Mail is the scene linked above, when we see how close Kathleen and Joe come to meeting on their daily walks to work. I love Kathleen’s scarf. I picked up a similar one in Edinburgh several years ago. The cashmere is so soft and has held up so well to daily use in the fall and winter.

A sleeveless dress

Kathleen wears several sleeveless dresses layered with her turtlenecks throughout the film–while “jumper” feels a bit juvenile a word to use, it’s always been a favorite look of mine. I love this dress from ME+EM, which has the exact look of something from Kathleen’s wardrobe. I’m dying to get my hands on it!

The photo in this post is from You’ve Got Mail, dir. Nora Ephron. I don’t own the rights to this image. As always, all affiliate links are marked with an asterisk. I only link to items I own and love. Thank you for supporting Fewer & Better!

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