Dressing Like Your Favorite RomCom Characters: Kathleen Kelly

Kathleen Kelly outfitsPIN

Recreating twelve of Kathleen Kelly's outfits from You've Got Mail

If there is one romcom that is the epitome of fall, it’s You’ve Got Mail. Every year on September 1st, I sit down to rewatch this movie for the umpteenth time. It has early 2000’s nostalgia, an adorable children’s bookstore, fall in New York (swoon!) and a charming yet quirky cast. Ah, I love it!

The second post in my new series (check out Lucy’s outfits from While You Were Sleeping here!), I’m recreating twelve of Kathleen Kelly’s outfits. Her style is relaxed yet chic. The range of clothes in her wardrobe is quite small and is mostly made up of cashmere cardigans and sweaters, pencil skirts, black low heeled shoes, and some easy loungewear. She usually wears very little jewelry and light makeup although she did sport some diamond studs and a berry lip to a dinner party once. Her very famous haircut does most of the heavy lifting in her overall look (and from what I read, it took a lot of work to maintain!)

In order of appearance…

Kathleen Kelly outfit with a white button down, black sweater vest, gray skirt, and black loafers

When Kathleen Kelly is working in her adorable little bookstore, she’s usually wearing a skirt, tights, and black shoes, typically with some kind of sweater on top. Here, it’s a black sweater vest layered over a sharp white button down.

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Kathleen Kelly outfit with a black turtleneck under a green jumper with tights and black shoes

If I owned a bookstore, this is what I would wear, too - a black turtleneck under a jumper and tights.

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Kathleen Kelly outfit with a knit turtleneck, black skirt, and black shoes

This might be my favorite look of the whole movie - an all black ensemble fancy enough for a dinner party where a caviar garnish is being served, ha.

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Kathleen Kelly outfit with a gray sweater, black pencil skirt, black oxfords, and a black peacoat

Here is what Kathleen Kelly wears when she’s shopping at Zabar’s - a gray cashmere sweater layered under her go-to peacoat (she wears this several times in the film), a black skirt, tights, and what I’m assuming are her usual black oxfords.

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Kathleen Kelly outfit with a blue sweater and long skirt

Kathleen usually sticks to neutrals but she added a little color for a Thanksgiving celebration with friends. Her sweater collection is on point! For this scene, she’s wearing a light blue sweater and long skirt. I can’t tell what footwear she has on so I took the liberty of adding what I think would be a good shoe for this look - some low heeled ankle boots.

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Kathleen Kelly outfit with a white tee, gray hoodie, and pajama pants

Kathleen is usually in some kind of smart casual look for work. but, at home, she’s often wearing a simple tee and hoodie with some comfy pants and warm socks.

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Kathleen Kelly outfit with a white tee, navy hoodie and gray sweatpants

Loungewear look number two for the ‘Go to the mattresses’ scene!

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Kathleen Kelly outfit with a tan sweater set, black skirt, and black kitten heels

This is a chic look with a tan sweater set paired with her usual black skirt for coffee date. Rose and book not included, iykyk.

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Kathleen Kelly outfit with a blue striped pajama set and trench coat

I know no one would actually wear this outfit (a trench coat over pajamas?), but this look is so iconic, I couldn’t not recreate it.

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Kathleen Kelly outfit with a white tee, tan cardigan sweater and pleated skirt

Here, the cardigan from that sweater set is worn with a pleated skirt for a spring day at the outdoor market in New York.

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Kathleen Kelly outfit with a white tee under a gray cardigan, tan chinos, and canvas sneakers

This is probably one of the most iconic looks of Kathleen Kelly’s, and one you’ve probably seen on Pinterest. It’s a simple look that would be easy to recreate.

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Kathleen Kelly outfit with a beige dress, blue cardigan, and ballet flats

Apparently, this Marc Jacob’s dress was the only designer piece Meg Ryan wore in the film. This look is classic and feminine and romantic.

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Read More:
Dressing Like Your Favorite RomCom Characters: Lucy Eleanor Moderatz
RomCom Inspired Outfits for Spring

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