Poughkeepsie Journal 

Women Trust Gamble's Fashion Taste 

Darryl Gamble is on a mission. 

"I always want women to look pretty," he said. 

As owner of Darryl’s, a contemporary boutique in Rhinebeck and New York City, Gamble is doing exactly that—dressing his female clients in clothes that make them look good and feel great

"I like people and I like dressing people," Gamble said. "I think it’s a natural for me. I like to make people look good, feel good."

Gamble started working retail as a stock boy for women’s clothing store when he was 15 and living in Detroit. 

After graduating from college with a social sciences degree, he moved to New York City, where he worked for fashion retailers and wholesalers, eventually landing a job as manager of a failing Upper West Side clothing store. He paid close attention to customers’ tastes and before long was able to turn the business around. 

Business partner Edward Coviello said some customers would select clothes fro the sister shop in midtown and have [a] sales attendant send the items up to Gamble to approve before making a purchase. 

"They wouldn’t buy it unless Darryl told them it was the right sweather for them," Coviello said. 

The experience led Gamble to think he could open his own store, Darryl’s, which he did on the Upper West Side in 1986. About nine years ago, he opened a second Darryl’s in Rhinebeck. Gamble filled both stores with "things to make women look beautiful without being tricky or gimmicky,’ he said. 

Of those working in clothing, accessory, and general merchandise stores in the nation in 2006, people involved in sales-related occupations made up 65 percent of the industry, 41 percent of whom were retail salespeople. Those in management business and financial positions titaled 2 percent of the industry’s employment. 

Gambles' success as a retailer is about more than the styles he carries in his stores. How he sells the clothes matters too. "I’m a psychiatrist on the side," Gamble said, joking. In truth, he connects with his clients by listening carefully to learn who they are and what they want. 

Nancy C. Thomas, president and CEO of the Retail Merchants Association, based in Virginia, said many retailers begin their careers as part-time salespeople and work their way up to management positions.

"A lot of retail is truly on-the-job training," she said,

Retailers’ hours often are long, especially for business owners, with holiday seasons keeping many busy around the clock. Recessions, however, can take a serious toll on profits. 

"Retail stays in your blood," Thomas said. It’s very interesting. It’s the people factor. It’s the true feeling of wanting to help someone."

Angela Elder, director of the career development program for the National Retail Federation, said some small retailers need to have a diverse dkill set to manage various aspects of their business, such as staffing, store promotions, product discounts, and inventory. 

"This speaks to how retail can actually be a very exciting career field, because you can be a small-business owner, you can be an entrepreneur, or you can develop specialites within retail," she said, referring to, for example, a merchandiser or advertising executive for a larger chain. 

Some of today’s retailers, Elder said, work to coordinate events or trips for their customers to further connect them with their stores. Others are putting their employees in advertisements to let customers know how knowledgeable and personal their teams are. 

Gamble is seeing the connections he’s made with some of his customers trickling down to the second generation.

"Because we’ve been around for a long time, we’ve taken care of the mothers and now we have the daughters," Gamble said. "It’s great."

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The Highlands Current

The Art of Clothing

By Alison Rooney, Arts Editor

Longtime partners open third store in Beacon

By Alison Rooney

Darryl Gamble and Ed Coviello, the owners of Darryl’s, a women’s clothing retailer founded 33 years ago in Manhattan, have added a Beaconesque feature to their third boutique, which opened on Main Street in October: an art gallery.

Its latest exhibit, which will have a Second Saturday reception tomorrow (Sept. 14), features paintings by Beacon artist Catherine Welshman. In October, the store will highlight the work of Jack Fuller, also from Beacon.

Gamble and Coviello, longtime partners in life and work, stock what they describe as “classic, with a twist” clothing lines, with each store — the other is in Rhinebeck — tweaked to reflect its location. In Manhattan, it’s “a bit more evening wear, more professional looks,” in Rhinebeck it’s “a little bit more relaxed” and in Beacon, “even more relaxed,” Gamble says.

They decided to display art because the store, at 155 Main St., “wound up being right in the middle of all the galleries,” says Coviello. “I thought, Why not?”

The couple met 37 years ago. Gamble was managing a clothing store on West 72nd Street and was ready to open his own place. Coviello was a special education teacher.

“Darryl has a great personality — people really like him,” says Coviello. “The store he worked at had a branch on Madison Avenue. Customers would go to the Madison store, try things on, and have them sent to the West Side for Darryl’s approval. So, we thought we’d try it for ourselves.” They opened Darryl’s on Amsterdam Avenue on Dec. 20, 1986.

The business struggled through that first winter, but the spring brought customers. “I remember March 5, a Saturday,” Coviello recalls. “Women started coming in, saying, ‘I’m looking for a dress,’ one after the other. By May, we were doing all right.”

“At that time, the Annie Hall look was popular; more folksy things were big in those days,” says Gamble. “We went more feminine and classic. Not everyone looks good in a specific trend. The important thing is consistency, as well as the taste level. It’s about finding the right mix of  ‘a look’ and quality, price, fit, fabric.

“You have to know what your customer will respond to, what suits their personality as much as anything else,” he adds. “There’s a whole psychological level to figuring it out, without having a crystal ball.”

The men each rotate between the stores; Gamble spends most of his time in Manhattan. They became acquainted with the Hudson Valley in 2006, when they bought a summer home, and later moved north year-round. They opened the Rhinebeck store a decade ago.

When they began considering Beacon for a third store, they feared they had waited too long. “We saw Main Street go from a lot of vacancies to few vacancies to no vacancies,” says Coviello. But a spot on the west end formerly occupied by Nella’s Bellas boutique became available.

“The biggest challenge is getting people to know us,” says Coviello. “We carry sizes 2 through 18, and if we don’t have a particular size at one location, we can easily get it in a day or two.” Their stock, which includes many pieces from Joseph Ribkoff (Canada) and Lyssé (France), consists of separates — skirts, pants, blouses — along with coats, dresses and accessories like scarves, handbags and jewelry.

Gamble says the partners have had success at home and work for more than three decades because of communication and the fact “we share the same work ethic, which is basically work, work, work. In any business, it takes time to be established. You have to give it a lot of love, a lot of hours. Plant a seed, water it. We want people to enjoy it as much as we do.”

Side note: Darryl’s has since closed the Beacon store to focus on its flagship New York City store and Rhinebeck, New York, store.

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A Little Beacon Blog 

Darryl’s Women’s Clothing Boutique

155 Main St., Rhinebeck, NY

Black Owned Business

Darryl’s Boutique hails originally from New York City on W. 84th and Amsterdam, and opened a second location in Rhinebeck. The store’s co-founders, Darryl and Ed, are residents of Wappingers Falls, and they wanted to join the Beacon community with a shop filled with fashions contemporary women will enjoy and find useful in their wardrobes. “We assist women in finding what suits them best, whether it’s for career, a special occasion, or casual wear. From wonderful knitwear from Spain, to perfect pants + jeans to flatter every shape, to the occasion dress and workwear.“ 

Spring Fashion Bounces Back With Bright Colors

By Bonnie Eissner

Spring 2021 fashion is about color and comfort, say retailers on New York’s Upper West Side.

According to U.S. Census Bureau data, retail clothing sales in March 2021 rebounded to pre-pandemic levels, rising more than 18% over February and nearly doubling since March 2020. Darryl Gamble, co-owner of Darryl’s Boutique, said sales in his store, which caters to professional women in their 30s and older, are slowly coming back. He and other Upper West Side retailers spoke about the fashions that are finally moving off their racks and shelves after a long, bleak year.

Spring sales in Gamble’s store typically spike around Passover and Easter. He and his partner Ed Coviello saw that trend return this year. “People have started to go to events, so they’ve needed dresses that hadn’t sold in several months,” Coviello said.

“People are also looking for color,” Gamble said. “New Yorkers are always in black and navy and dark colors, and they’re coming out, and they’re asking for color. They want to be lifted.”

Michael Feinman, a regional manager at Goodwill Industries of Greater New York and Northern New Jersey, who oversees 10 thrift stores, including one on the Upper West Side, said his customers have similar tastes.

“There’s such a need for lots of bright color,” Feinman said. “My take on it is we sat in this dark period. The winter was miserable. And now that the sun’s out, people are really embracing color and fast fashion in such a way that I haven’t seen since my days back with Bloomingdale’s.”

Comfort is also big.

“We’ve inventoried more casual, more relaxed,” Coviello said. He described the dresses that are selling as flowing and easy, less structured and formal. Tops are in higher demand than pants, as his customers are primarily being seen from the shoulders up on Zoom calls.

This spring, Gamble said, women are wearing wider cropped pants. “The legs have gotten a little fuller,” he said.

Feinman is seeing “a lot more casual looks going out the door” for men, too. Popular men’s items, he said, include “twill, denim, collared shirts, button-up shirts, great graphic tees.”

Upper West Side resident Deborah Meer, 48, spent part of Saturday, April 17, shopping at Tip Top Shoes on 72nd Street for some comfortable shoes that would hold her orthotics. A compliance officer at JPMorgan Chase and mother of two, she has been working at home since March 2020. She found a pair of low-heeled, mesh Merrell clogs, the Encore Breeze 4, that fit the bill. It was her first shoe purchase, other than sneakers, in at least a year.

She last bought clothes for work over a year ago.

“I'm really only looking to wear new clothes when I think I'm going to be seeing people,” she said.

“When I know I'm just going to be working at home in front of a screen, I don't think people care if they see the same shirt on me every week.”