By Meg A. Parsont

Many years ago, when I needed a last-minute interview outfit, I went to Darryl’s at 492 Amsterdam Avenue, between 83rd and 84th streets. Co-founder Darryl Gamble pulled a dress off the rack that, to be honest, I probably wouldn’t have tried on without his encouragement. I purchased it and yes, I got the job. Years later, when I needed a dress for a gala, I headed over to Darryl’s, having no idea what one even wore to a gala! I fell in love with a 60s-style dress that I’ve since worn to weddings and other special occasions. Each time, I delight in the fact that it’s different from the cookie-cutter little black dresses on many of the other guests.

Since he opened Darryl’s in 1986 with his partner Ed Coviello (whose middle name happens to be Darryl), Darryl Gamble has come to the sartorial rescue of three generations of customers. His original customers in the mid-80s—women who were likely to buy a blazer or tailored suit with shoulder pads—are now bringing in their granddaughters who are on the lookout for jeans and fun tops. Chances are, they’ll both leave the store happy. Darryl’s carries a wide range of clothes, from special occasion dresses embellished with a bit of bling to leggings and sweaters. And unlike most other boutiques, Darryl’s makes it a mission to offer something for everyone and stocks up to size 16.

Styling others comes naturally to Gamble. As a child growing up in a close-knit family in Detroit, he often selected items for his mother when they went shopping. His brother and three sisters were also receptive to his styling suggestions and later, when one of his sisters had seven children of her own, there were countless opportunities for family styling! He reflects, “My parents were both clothes horses, which is probably where I got it from.”

When Gamble was growing up, his mother regaled him with stories about when she lived in New York City in the 1940s. He decided to move to New York City after college and arrived here in the late 70s at a time when pioneering stores like Charivari and trendy restaurants were starting to put the Upper West Side on the map. He worked at Stewart Ross’s Stone Free clothing shop on West 72nd Street which he describes as “very Annie Hall.” Gamble turned the floundering Upper West Side shop around and made it profitable.

He and Ed Coviello, an educator who learned the ropes of retail at the West 72nd Street store, decided they were ready to open their own boutique. They knew they wanted to stay on the Upper West Side, where Gamble already had a large and loyal customer base. They could never afford rent on trendy Columbus Avenue, and Broadway was too big for the shop they had in mind, but they could afford the rent on Amsterdam Avenue. They opened on December 20, 1986 in the storefront that is now the Magpie gift shop. Then they moved up the street to their current location at 492 Amsterdam Avenue, where they occupy two storefronts.

Their decision to open on Amsterdam Avenue paid off. Coviello explains, “We became the neighborhood shop where people could come in, buy their dress, go home, and have the rest of the day to themselves. They didn’t have to go schlepping down to department stores or other shops.” 36 years later, Darryl’s is still a true neighborhood boutique that has flourished over three-plus decades and made it through the pandemic.

Gamble says, “We have incredible clients. During Covid, we had customers checking in on us to make sure we were okay. Everyone was so supportive.” Coviello adds, “We had clients who would come in and buy a gift certificate for themselves, even though they didn’t need anything at that time. They figured they could always use it later.”

The Darryl’s co-founders note that, post-pandemic, there’s renewed energy in the store as people have returned to work and are going to more special events again. But everything is more casual now, and the racks of the shop reflect people’s changing needs and tastes with more separates and sportswear. What hasn’t changed is the comfortable, calm shopping atmosphere at Darryl’s and the personalized attention customers receive. Gamble reflects, “I think a big reason why we’re still here is that I match the person to the clothing. I take into consideration their demeanor, whether they seem to be receptive to color or not, and work with them to find the item best suited to their personality.”

When I was in Darryl’s recently, a woman came into the shop on a mission to buy a blouse. She went into the dressing room with an armload of options but was having a Goldilocks moment. One was too big, one was too long, one was too short. She was on the verge of leaving empty-handed, but agreed to try on a blouse that Gamble had picked out for her, and it was just right. Yet again, he had worked his styling magic.