Meg Ryan’s Best Outfits in ‘You’ve Got Mail’

Many laud the sartorial magic made when Meg Ryan worked with Nora Ephron on rom-coms set amid the falling leaves. A perfect example is You’ve Got Mail, which follows independent bookstore owner Kathleen Kelly (Meg Ryan) and chain bookstore owner Joe Fox (Tom Hanks) as they go from public enemies to internet pen-pals then lovers. But the best part of You’ve Got Mail isn’t the romance—it’s Meg Ryan’s outfits.

It’s no wonder that ‘90s Meg Ryan style appreciation posts are rampant now that the decade’s dress is back in full force. Featuring turtlenecks and layered knits and sweater sets, You’ve Got Mail showcases Ryan-meets-Ephron film fashion at its best, and that’s all thanks to costume designer Albert Wolsky. Wolsky has worked on Grease, Sophie’s Choice, Runaway Bride, Maid in Manhattan, Across the Universe, Birdman, and many more. Ahead, we speak with Wolsky about what went into Meg Ryan’s outfits in You’ve Got Mail. Keep reading for six of her most iconic looks.

A Button-Up and Sweater Vest

For her first look in the film, Kathleen wears a gray pencil skirt, a crisp white button-up with a flat collar, a black sweater vest, and her signature Oxfords and tights. While outside, she layers with a boxy black coat, patterned scarf, and a tote that reps her indie store, A Shop Around the Corner.

When discussing the character’s more conservative fashion, Wolsky explains, “You have to go back to those times. I was trying to dress her not necessarily conservatively, but she was running a bookstore, and I tried to make her a bit more studious…There’s nothing about her that was fashion-y. Versus Parker Posey in the movie, who plays a fashionista.”

The Layered Jumper Look

As Kathleen discovers that a Fox Books is opening up in her neighborhood, she’s wearing a black turtleneck underneath a green-gray jumper dress that’s topped with an oversized cardigan. She pairs this with her black Oxfords and matching wool tights.

Though this jumper looked fantastic on Ryan, Wolsky reveals that he had trouble getting her to wear the look. “I never understood [why she didn’t like jumpers],” he stated. “For her—although I think it was perfect and looked wonderful—it was maybe too schoolmarm. I think she felt too straight-laced, if you will. Even though none of the clothes are not straight-laced.” How’d he solve that character conundrum? “It’s okay because you have to listen and work around it. It wasn’t that she was being difficult. It was just something about that look that wasn’t working for her.”

Oxfords and Black Tights

Throughout You’ve Got Mail, Meg Ryan wears black wool tights paired with black Oxfords or ankle boots. It happens so often that we had to ask about it.

“I love to repeat clothes. There are things that [Kathleen] wore once and then wore with something else again, which is the way people dress,” Wolsky stated. “To me, [the tights and Oxfords], that was very New York. It’s a New York movie.” The designer added that working with Nora Ephron on this film was especially dreamy because she was a true New Yorker who understood the city’s character and geography.

The Mock-Neck LBD

While at a party with her boyfriend Frank Navasky (Greg Kinnear), Kathleen wears a mock-neck little black dress with above-elbow sleeves. She accessorizes with only a pair of gold stud earrings. Even more than 20 years later, this outfit wouldn’t look out of place at many New York City celebrations. But for Kathleen, it was a look—and one she likely wouldn’t repeat.

“That was [the character’s] version of dressing up,” said Wolsky. When asked if this dress would make a welcome Thanksgiving ensemble, he added, “The first outfit would be fine. I think [this] dressy dress…that would be too dressy for Thanksgiving.”

Wide-Leg Trousers and Cardigan

To keep up with Kathleen’s utilitarian vibe while she’s walking around New York with Joe, Wolsky put Ryan in a pair of wide-leg khaki slacks with a brown belt, a white T-shirt, gray cardigan, and a pair of neutral sneakers.

“If you’re looking at [this] character, who she is in the film, it doesn’t change that much,” Wolsky said. “[Kathleen’s] always the same person. She has a T-shirt, a sweater, slacks—which are just plain slacks [with no designer name]. They’re not jazzy or fashion-y.”

The Central Park Dress

Kathleen’s final look in the film, the boatneck Marc Jacobs dress she wears when kissing Joe in Central Park, required more work than it seemed.

“The only [clothing] that had a [designer] name was the last outfit,” said Wolsky. “We loved that dress, but I had to dye it slightly and add a slip underneath because it was totally transparent.” When asked about the character’s ballet flats, the designer added, “They were not designer shoes. They were Forever 21-type shoes. But they worked with the dress.” After all, the iconic Kathleen Kelly definitely would’ve been dressing on a budget; still, she never compromised on style.