Nancy Pearlstein, left, with niece Laura Pearlstein Mills. Pearlstein opened Relish boutique 20 years ago. She hopes to hand over ownership to Mills in the coming years. The high-end clothing store in Georgetown is among a shrinking number of independent clothing retailers in the country. (April Greer/For The Washington Post)

A thin, dark-haired woman in ivory-colored chinos and black boots walked into Relish, the high-end clothing boutique in Georgetown’s Cady’s Alley. She was on the prowl for something: a dress, an extra helping of confidence, an amusement. Rarely do shoppers who wander into stores such as this know precisely what they’re looking for until they see it.

“With high fashion, you’re creating demand,” said Nancy Pearlstein, the owner of Relish. “The first thing you have to have is taste. And then that taste has to be commercially viable.”

In a sophisticated and vaguely aloof environment, Relish sells from-the-runway fashion: Dries Van Noten, Sacai, Thom Browne, Marc Jacobs, Veronique Branquinho, Marques ’ Almeida, Simone Rocha. Her customers are careerists and philanthropists, suburban mothers and urban singles. Women for whom one dress is an extravagance, as well as those who can spend thousands of dollars at once.

Before she set up shop in Washington in 1996, Pearlstein asked a small group of local women what they thought a successful clothing boutique would look like. She based her stock on their suggestions, “but I also bought things they hadn’t talked about,” Pearlstein said. “When it came to what sold, it was what they didn’t mention.”

Since then, Relish has been defined by Pearlstein’s singular point of view. She loves classic silhouettes rooted in menswear. She appreciates the cubist sensibility of more experimental brands. She has a soft spot for plaid. The stock is not for everyone’s taste. But for those it pleases, it pleases them greatly.

“That’s what makes every specialty store look different,” Pearlstein said. “You’re not trying to appeal to everybody; you’re trying to appeal to everybody with the same sensibility.”

Relish is the kind of store that was supposed to have disappeared under pressure from department stores, e-commerce, cultural shifts and a recession. It focuses on one-to-one styling. And it delivers the sort of tough love an algorithm cannot: the willingness to tell a client what she should not buy as well as what she should.

And it is thriving, in a town better known for its love affair with power dressing than creative edge.

Now, as the store marks its 20th anniversary, Pearlstein is pondering these questions: How does an independent boutique like Relish continue to grow and flourish? Will her young niece, whom she has welcomed into the business, carry on her legacy? Will Relish be able to make the next generation swoon?

The clothes at Relish are not overtly frilly or obviously sexy. They are attentive to fashion trends but not beholden to them. (April Greer/For The Washington Post)

For the shrinking ranks of independent clothing retailers, selling a single frock remains a time-consuming but rewarding endeavor. “I still believe in the power of a conversation with a client about her life,” said Susan Foslien, who owns Susan in San Francisco. “And then she can go out and live that life.”

That philosophy recalls an era when merchants knew clients by name and a sale took place only at the end of a season.

But customers have changed, as has the amount of time they’re willing to spend inside a store.

Relish still hosts a sale only twice yearly — in June and January. It does not sell merchandise online. It’s closed on Sundays and Thanksgiving Day. At Relish, the customer is not always right.

I asked Pearlstein, a friend and colleague of many years, to let me watch her in action. As a merchant, she is unbound by spreadsheets and attentive to her own gut feelings, which have led her toward upstart labels and off-kilter creativity — and in turn drawn more daring customers.

It took about five years for Relish to build a customer base, first in its original Chevy Chase location before it moved a decade ago to its sprawling 6,000-square-foot space in Georgetown. Once the store found its footing, it saw double-digit growth, Pearlstein said.

These are challenging times for retailers. Department stores such as Saks Fifth Avenue and Neiman Marcus saw sales drop last year. Ralph Lauren has been closing stores and reducing inventory. Even Chanel and Hermès have seen sales slow.

More consumers now swear by online shopping, where they can dodge sales tax and hunt for the best price. Luxury consumers “come in here and have someone help them. Then they’ll take all the information and go home to find [a garment] online for less money,” said Karen Daskas, co-owner of Tender in Birmingham, Mich.

After the economic downturn, some specialty stores hooked their wagons to larger corporations. Others shrank their footprint. Some retailers simply burned out. Relish felt the recession, too, Pearlstein said, but by the second half of 2010 was back on track.

The forces that pressured fashion’s specialty stores are similar to those that threatened independent bookstores, which survived by making themselves part of the civic fabric. So have fashion boutiques, which have forged closer ties to both customers and designers. And many have been rewarded.

“When we were little-known, being discovered by the owners and buyers of specialty stores such as Relish, Ikram [in Chicago], who have great appreciation for fashion and the support of their selective clientele, nurtured the brand,” said Sacai designer Chitose Abe, who is based in Tokyo. “Our business has grown quite steadily and organically thanks to the love and support from these specialty stores.”

In return, Abe said, she has been careful to curtail her sales among online-only retailers — “to protect brick-and-mortar business.”

Pearlstein, right, with customer Jennifer Peacock, would like to translate her aesthetic and brand of slow fashion to the fast-paced digital world without losing its integrity and intimacy. (April Greer /For The Washington Post)

Pearlstein, 62, is a slim, athletic woman with curly blond hair who is both blunt and precise. She can be charming and infuriating — all in a single Boston-accented sentence.

The Brookline, Mass., native majored in physical education at the University of Colorado, then went to work at Louis Boston, the clothing store founded by her grandfather in 1929 and transformed into a fashion leader by her late father, Murray Pearlstein.

She introduced womenswear to Louis before leaving to work at the larger, more conservative Mark Shale in Chicago. Looking to open her own boutique, she moved to Washington at the urging of her brother, Steven Pearlstein, an economics writer at The Washington Post. (Her sister took over the family business, which closed in 2015.)

The clothes at Relish are not overtly frilly or obviously sexy. They are attentive to fashion trends but not beholden to them. Consider last season’s “must-have” furry shoe:

“I did a Velcro sneaker that has fur under the Velcro, which I thought was a very chic way to do it,” she said. “I was going to buy other shoes, the slipper, the whole look.” But then, “I was seeing it so much I thought, ‘I don’t want to do it.’ ”

One recent afternoon at Relish, Pearlstein was unpacking an order from Dries Van Noten. It was a box of tan suede sandals with a shiny, decorative disk and matching glossy platforms. Lovely, but wrong: They were supposed to be matte leather with no disk.

Pearlstein was hesitant to send them back, which could hurt her relationship with the designer. “When I complain, I want to be correct. If I made the mistake, that’s the end of the conversation.” It was her mistake. She kept the shoes and never said anything to the designer. The sandals didn’t sell. “The style I wanted would have sold better,” she said.

Issues with fit are a bigger problem, she said. Last year, an order of shrunken sweaters couldn’t fit even her smallest customer. So they were sent back. But now, clothes are gigantic again. It will take time for customers to adjust to this new silhouette. Pearlstein will have to help them see themselves in a new way.

“Take oversized jackets. I bought them for [last] spring from Marni. I sold a couple of them. They’re not the easiest sell,” she said. “But I want to buy it and give the customer something new. Something I believe in.”

What makes a $2,000 dress? The label. The fabric. The finish. Handwork done in Europe, where labor costs are higher but the quality is better than in China. “It helps to have someone explaining the idea of the brand and justifying the price,” said Marie-Christine Statz, founder of the young design house Gauchère. At larger stores, the sales staff “don’t know the meaning of the brand or what kind of fit is right.”

Is any dress worth so much money? “Who am I to say?” Pearlstein said. After all, is any car truly worth $200,000? But the idea that a customer would wear a special-event dress only once — a notion popularized by fashion fanatics who Instagram their lives as if they were celebrities on a red carpet — is anathema to her. “If I love it, I’d wear it every chance I got.”

There’s a stereotype that the sort of woman who spends more than $1,000 for a dress must be a trust-fund baby or a narcissist. But Relish customers are curators and gallerists, real estate developers and financiers, as well as government officials and holders of White House hard passes.

A New York-based curator — a tall woman with cropped gray hair who didn’t want to share her name because she was not supposed to be shopping during this business trip — discovered Relish a decade ago. “I don’t like to have a lot of clothes; I just like things that are beautiful and classic,” she said.

Pearlstein would like to translate her aesthetic and brand of slow fashion to the fast-paced digital world without losing its integrity and intimacy. She would like to reach millennials by showing them that fashion retail can be a creative and memorable experience.

That next-generation challenge will fall to her niece, Laura Pearlstein Mills, 31, who recently began working at Relish after 10 years in advertising and branding. Mills is learning about the merchandise, working with customers, getting to know the fundamentals of retail and considering how to expand her aunt’s singular vision.

“We’ve come of age when high-end fashion has been commoditized. It’s all point-and-click,” Mills said. The real challenge is to take what’s so special about personal interaction and figure out how to scale it.” Millennials do care about the personal touch — “it just hasn’t been presented to them when it comes to shopping.”

Pearlstein pulls garments for Peacock and awaits feedback. (April Greer /For The Washington Post)

That dark-haired woman — the fashion hunter fingering the merchandise with curiosity — finally explained that she wanted something to wear to lunch in New York. She already has a closet full of clothes. And this wasn’t a meal upon which her professional reputation or social stature depended. The quest for fashion is rarely that dire.

“What do you do with a dress like that?” she asked, pointing to a black jersey Joseph tunic priced at $650.

Belt it, perhaps, or wear it with a jacket, Pearlstein explained: “I think it’s appropriate for what you’re trying to do,” she said.

The questions kept coming: What kind of shoes do you wear? Could she wear white? Is it too early for that?

The woman left empty-handed. Counseled but uncommitted.

Robin Givhan is The Post’s fashion critic.