What Does a Cool Girl Look Like?

There is a certain look that a certain type of person strives to achieve when getting dressed: composed, distinct — no one else is wearing this outfit — without trying too hard.

She may be wearing something just edgy enough to catch eyes but not turn heads. The style is a kind of camouflage, in that she rarely looks out of place, never overdressed nor underdressed. There are endless interpretations of this aesthetic, and endlessly subjective words used to describe it, like “chic,” “effortless” or “put together.”

But lately, the reigning phrase used to describe this look — the one often deployed by marketers and media to sell this look — is “cool girl.” And in American fashion right now, the label most often associated with “cool girl” is Khaite.

This is, in some ways, a mystery to Catherine Holstein, who founded the brand in 2016. But that’s the cool girl way; a true cool girl would never describe herself as such.

“First of all, you’re asking the most self-loathing person — I’ll find something wrong with everything,” said Ms. Holstein, 38, who in November was named women’s wear designer of the year by the Council of Fashion Designers of America, an award for which she had genuinely prepared no acceptance speech.

“The ‘cool girl’ thing I don’t agree with so much,” she said. “It’s a very youthful term. I won’t say it’s bad, but I think we have a lot more range than that.” (Khaite’s average customer, according to its data, is between 25 and 34.)

Ms. Holstein hopes this narrative will change, she said, with the company’s next phase: opening its own stores and thereby gaining some control over the environment in which the line is presented. Currently, Khaite is carried in about 270 stores or websites globally, where its top sellers tend to be leggy jeans, sexy-ish knitwear, or heeled boots and tote bags in rich, high-quality leather. Emphasis on rich. Other than denim, which starts around $420, prices for a piece of Khaite’s clothing typically exceed $1,000.

Its first store, scheduled to open Thursday in SoHo, is an austere space punctuated by curved steel structures, à la Richard Serra. It is mostly gray, except for large carpeted dressing rooms in Stanley Kubrick red — “the right kind of red, not too orange, not too burgundy,” said Griffin Frazen, the architect, who is also newly married to Ms. Holstein.

The store aims to capture the same qualities of Khaite’s clothing: sleek, self-assured, a little gothic-romantic. And, in spite of Ms. Holstein’s protests, cool.

Building a Mystery

“Have you ever seen ‘Friends With Money’?” Ms. Holstein asked. Her film references run deep. She was sitting on a black leather sofa, overseeing fittings for her runway show. “Frances McDormand plays this luxury fashion designer — she has a very expensive fashion line at Barneys — who stops showering and only wears her pajamas everywhere. She’s not descending into madness or anything, she just stops caring. I always joke that I feel like that’s me now. I love clothes and I love shopping, but everything has to be very easy.”

Ms. Holstein wears little makeup. She parts her smooth chestnut hair down the center, pushed behind her shoulders like an afterthought. She dresses casually, too: a Khaite sweater or cardigan, thick and soft, over loose pants. Although her recent preference for elastic waistbands is more related to her being, at time of this writing, nine months pregnant.

She was drawn to fashion from a young age, when she would copy fashion sketching templates belonging to her older sister. She dressed boyishly as a child, emulating her brothers, yet “had infatuations with really feminine girls in my class, who dressed really frilly.”

As she got older, she’d steal luxury designer pieces from her mother’s wardrobe and gradually acquired her own: a Dior bag for graduation, a beloved Nicolas Ghesquière-era Balenciaga leather jacket for Christmas in her 20s. Her father worked in finance, and the family moved from Connecticut to San Diego to London, where she spent most of her youth, then back to California just before Ms. Holstein finished high school.

She came to New York to attend Parsons, where, during her junior year, she designed a collection of six sailor dresses. After Teen Vogue spotted the dresses at events around the city, the magazine brought her in to show the collection to editors. One editor tipped off Barneys, which placed an order. Ms. Holstein dropped out of school to start her namesake label.

“It was a very privileged place to be in, of course, in terms of having that access,” she said.

When the recession hit, Ms. Holstein decided to close the business rather than struggle through it. She took various jobs in fashion, including stints in top design roles at the Gap and Vera Wang, followed by consulting at J. Crew and the Elder Statesman.

But on the cusp of 30, Ms. Holstein began to feel discouraged, as if she’d missed her chance to move to Paris and work in a more traditional luxury environment. Then, she said, a friend intervened, telling her over dinner that he believed she could run her own company again. That friend was Charlie de Viel Castel, one of Khaite’s early investors, who is now married to Khaite’s longtime style director Vanessa Traina, whose sister Victoria was in the same Parsons class as Ms. Holstein. (The Traina sisters are the daughters of the couture-loving novelist Danielle Steel.)

From there, and with capital from the group Assembled Brands, Khaite was born. The idea was primal for Ms. Holstein: to make clothes that could last forever, she said, like the ones in her mother’s closet, and that could “make you better understand yourself.” She saw fashion as an “identity builder.”

Not that she’s particularly comfortable sharing her own identity with the world. Many designers link their personas with their brands, acting not only as creative director or chief executive but as physical embodiment. (In American fashion, Ralph Lauren is the blueprint.) But Ms. Holstein has shied away from being the public face. She hopes to replace herself as chief executive later this year, to focus more on being the creative director. (“It’s just not wise — I’ve never taken a brand beyond $100 million,” she said. “I know my boundaries.”)

Her reticence comes largely from that self-loathing she mentioned. Ms. Holstein talks quite openly about living with insecurity. Even the idea of having hair and makeup done for the CFDA Awards seemed to her embarrassingly fussy. She was expecting to lose, anyway.

Yet she also recognizes that privacy can beget mystery — a commodity in an industry that breeds extroverts.

“Some of the best fashion designers, like Phoebe Philo or Hedi Slimane, are notoriously private,” Ms. Holstein said. “I can only speak for myself, but you want to make sure that the clothes have their own platform, and that it’s not too much about you. Even though it so is.”

Street Style

There is an obvious irony in Ms. Holstein, who is so forthcoming about her own shame, producing clothing so associated with confidence. (“I kind of hate that word,” she said. “Who’s really confident?”)

For Alison Loehnis, the interim chief executive of Yoox Net-a-Porter group, which has sold Khaite since 2017 — and said it is one of Net-a-Porter’s fastest growing brands within its categories and price point — the word that comes to mind is “nonchalance.” The Khaite woman “cares but doesn’t care too, too much.”

It’s that “cool-girl factor,” she said. “A woman who is comfortable in her own skin, who walks in the door, head held high, curious.” One of Khaite’s most familiar images is a viral paparazzi photo of Katie Holmes hailing a taxi in a matching cashmere bra and cardigan falling casually off one shoulder.

Kendall Jenner, too, said she appreciates Khaite for “that cool girl-walking-around-the-streets vibe.”

More looks from the fall 2023 collection.Credit…Photographs by Celeste Sloman for The New York Times

“It just feels like my vibe, in a sense that’s hard to explain,” said Ms. Jenner, who is indeed a cool girl who walks around the streets, but also a creative director of the online store FWRD, which sells Khaite. “When something feels like you, it just can’t help but feel good.”

Yet there is a reason people more often describe the feelings Khaite evokes, rather than the actual fashion. The design is not necessarily groundbreaking; the clothes are “stealth,” as Ms. Holstein has said. Unlike other designers, her priority, and that of her creative partner, Ms. Traina, is not to make women look as beautiful as possible, as if they’re living in a fashion fantasy.

Their woman must exist in reality (at least a reality where she can both afford the prices and fit into the size range). “Is this character believable?” Ms. Traina emphasized last Thursday, while fitting models ahead of Sunday’s show.

“When you look at the board,” she continued, gesturing at a big white plank jabbed with photos of each outfits in progress, “I could imagine sitting in a restaurant, or seeing any one of those looks walk down the street on the woman, and feeling immediately drawn to her.”

One of those looks, as presented at Khaite’s runway show, was an oversize blazer worn over a long sheer chiffon skirt, streamlined and stiff on top, swishy and sexy on the bottom.

“You could be that person,” Ms. Traina said.

“It’s achievable,” Ms Holstein added. “When it’s such a fantasy that you can’t see yourself in it, then is it really that desirable?”