How Darien Sport Shop Built an Institution Over the Past 80 Years

Stephen Zangrillo may be gone 11 years, but his loyal customers still remember him as a fixture at the front door — always in a three-piece suit — greeting them and passing out lollipops to their children.

Zangrillo, known simply as Mr. Z, was the founder of the Darien Sport Shop in Connecticut. Run today by his daughter Gina Zangrillo, the store he started in 1946 has grown into one of the most respected multibrand specialty retailers in the country.

Born and raised in Darien, Stephen Zangrillo served in the U.S. Army during World War II and was stationed in the South Pacific. When he returned to Connecticut, he got a job at Pitney Bowes in nearby Stamford — without a car, he had to hitchhike there and back every day — and on the weekends, was a caddy at the local golf course, his daughter related.

“His dad was a roofer and one day, said to him: ‘What are you going to do with your life? Are you going to keep hitchhiking every day? You should open a store.’”

So without a retail background, the 22-year-old Zangrillo took that advice and found a small storefront of around 800 square feet on Post Road in his hometown and “sold whatever he could buy from the salesmen that pulled up and opened their trunks,” Gina Zangrillo said.

Those trunks held an eclectic assortment of products including tennis rackets, fishing rods, golf bags and men’s ties, dress shirts and suits. The sports products allowed him to compete against another local merchant, Bob’s Sports, but instead of naming his store after himself, he opted for Darien Sport Shop.

While the mix may have been incongruent, there was one thing Stephen Zangrillo excelled at: dealing with people. From Day One, he treated his customers like friends, knowing that if they had a pleasant experience, they would come back.

And come back they have, for 80 years.

A people person and an innate merchant, Zangrillo was also ambitious. “My father would come home every day and say, ‘I’ve got to get bigger. I’ve got to make the store bigger,’” his daughter said.

So in 1950, he moved across Post Road and doubled the size of the store. Four years later, he bought a two-story building on the same street and expanded again. By this point, he had also brought in some womenswear to complement the men’s, while retaining the sporting goods.

It was in 1963 that the store debuted its first ski shop, with the grand opening scheduled unfortunately on the day that President John F. Kennedy was assassinated. Those were also the days when merchandising wasn’t top of mind. Gina Zangrillo said the men’s department was far from pretty back then. “It was ‘pile it high and let it fly’,” she said.

Bigger and Bigger

In 1978, as Stephen Zangrillo continued in his quest to get bigger, he bought some land and three existing houses, built a 12,000-square-foot addition, tore down the houses and created a parking lot. He also significantly expanded the women’s department, bringing in all the hot designer brands of the day including Pierre Cardin, Gloria Vanderbilt, Stanley Blacker, Sasson, Izod and others.

But for Zangrillo, even that wasn’t big enough. When the gas station next door became available in 1996, he bought that too.

“The guy that owned the gas station knew that the day he wanted to retire, all he had to do was tell Steve Zangrillo, and he would write a check for whatever the guy wanted,” Gina Zangrillo said.

That allowed Darien Sport Shop to expand again to its current size of 45,000 square feet with distinct departments for menswear, womenswear, childrenswear, home, gifts, ski and sports.

In subsequent years, things changed dramatically and a lot of it can be attributed to Gina Zangrillo who joined the family business in 1994. Although she had grown up in and around the store, she couldn’t wait to leave town. From the age of 12 on, she and her three older siblings were required to work in the store after school and on weekends if they weren’t involved in a sport.

“When I was 16 or 17 years old, on a Saturday morning after going out with my friends the night before, I would go up to the ski shop, grab seven parkas off the rack, put them in a fitting room and take a nap,” she admitted with a laugh.

So it’s no surprise that after graduating early from high school, she left Darien at 17 to go to a two-year fashion college in Atlanta. “I couldn’t wait to get out — my entire life, I was the daughter of the owner of the Darien Sport Shop: the first day of school, fifth grade, seventh grade, that’s what all the teachers said. But I just wanted to make it myself.”

She said her parents were “livid, they didn’t want me to go, and said if I didn’t like it, I had to pay back every cent they spent.”

Turns out, they were absolutely right, she said. “It was the biggest mistake of my life, but I never told them, I stuck it out, I finished, and when I was done, I didn’t know what I was going to do, so I went to work for Rich’s, the department store chain in Atlanta.”

That lasted five weeks before she found herself “bored out of this world,” and left. For the next two years she worked for a company called WM Industries that she described as a “pyramid company,” selling jewelry door to door.

“I would walk into an office, dodge the security guards in the high rises in downtown Atlanta, and say to the receptionist, ‘Hey, listen, my boss is going out of business, he’s got this beautiful jewelry, he literally gave me everything, I have it in my car, I can’t go back to the office today. Everything’s $20. Do you want to see if any of the ladies in the back want to come out and take a peek?’”

She did well enough to eventually become a manager for the company, relocated to Houston and then San Francisco.

“It wasn’t great, so I went back to Darien for a visit and never left,” she said.

Her mother, a Canadian whom her father met in Bermuda during a golf tournament, married and brought back to the States, told her she needed to find a job. “Interestingly, Darien Sport Shop never even came up,” she said. “It wasn’t even suggested, which is so weird. I had no skills, I had a two-year associate’s degree — I couldn’t even type — but I went to a personnel agency and they placed me as a receptionist in a telecommunications firm in Greenwich.”

She quickly rose through the ranks and eventually began running the company’s trade shows and organizing its hospitality suites. “I loved my job, I was traveling all over the place, it was awesome.”

She continued to ascend within the company but in 1994, as she was just about to give birth to her second child, she stopped by the store to visit her dad, and that’s when everything changed.

“My dad was sitting out on a stoop because business was so bad, he walked up to the car door and said, ‘How’d you like to come work for me?’ And I said, ‘I have a great job, and I’m having a baby next week.’”

Bad Times

Her father had gotten very ill in 1992 and nearly died, but he managed to recover. The same couldn’t be said for the business at that time. The illness caused him to be out of the store for six months and by the time he got back, things had gotten so dire that the company’s accountant was just about to sell the company. “In all fairness, he was not a very good delegator,” she said of her father, “and it kind of left them all in the lurch.”

The company’s accountant was in the final throes of the sale when Mr. Z changed his mind and walked out of the room. Instead, he turned to his daughter to save the business. “He realized that I was the only one that had worked in the world for 12 years and understood things like employee benefits and 401ks.”

Although the accountant warned her not to go into the family business because her father was “so tough,” she decided to take the plunge. “I like challenges in life,” she said.

So one week after having the baby, she joined Darien Sport Shop.

The first thing she did was put in a computer system to replace the manual stock keeping that the store had been doing, hired a marketing agency that helped implement the store’s first loyalty program in 1996, and “evaluated the business one department at a time.”

By 1999, she was essentially running the company even though her father was still active.

Then she set her sights on the personnel, which included her uncle, brother and sister.

“My father built this from nothing,” she said. “He was a 22-year-old guy without anything but a high school education, and some people were not exactly working very hard and taking some liberties, and it really irked me.”

With Gina Zangrillo now in charge, her uncle and sister decided to leave the business and her brother stayed on for a few more years before eventually exiting as well.

“I was the bad guy,” she said.

So with that history, is Gina Zangrillo tough to work for too, like her father? She shrugged. “I’m not educated, all I have is growing up in the business and learning from experience. But I do believe in hard work and the school of hard knocks and learning from your mistakes, and if you don’t know how to do something, find out.”

So while she may have taken a lot of heat for her decisions, the results speak for themselves.

“I quadrupled the volume,” she said of the store, whose sales are estimated at around $20 million.

When she took over, she said Darien Sport Shop was “like a pretty picture, but the frame was broken. One thing I learned in life is that if you surround yourself with successful people, you will be more successful, and I have gone out of my way to hire talented people.”

Adding Talent

She said her father had been buying the womenswear until he was 82, but she finally hired a buying office and eventually a women’s buyer. “My father was a born merchant, but I’m not sure I was,” she said. “What he was really good at was just watching people. He would see ladies walking in with Burberry handbags and realized, we’ve got to get on this Burberry thing. He just followed trends by watching people and talking to people.

“A lot of our clientele vacation in Nantucket and Martha’s Vineyard every summer, and the minute those ladies were back, Mr. Z had them cornered: ‘What’s hot on the Vineyard,’ he would ask, because he knew whatever was hot there was going to be hot here. He was very good at that.”

And what Gina Zangrillo is good at is making tough decisions.

Although sports equipment has been a hallmark of the business since it started, it doesn’t turn as quickly as apparel. Initially, the sports department was located on the main floor, but in 2007, Gina Zangrillo went to her father with a fact that would change the trajectory of the store.

“I walked up to him and said, ‘Hey, Dad, the men’s department is doing $1,500 a square foot and sports is doing $300. I need to move it to the third floor.’”

They did, and now, men’s and women’s apparel is on the main floor while the upper level is chock-full of skis, boots and other winter sports gear during the winter and blow-up pools, yard games, tubes, rafts and beach toys in the summer.

Gina Zangrillo’s second son, Doug Reilly, is the latest family member to join the business. He started in the spring after working at a hedge fund in Stamford and serves as general manager. For around four years, his older brother Greg had been with the business, first as marketing manager — he joined in 2020 to help with the store’s 75^th anniversary celebration — and then took on men’s buying responsibilities.

“He did an outstanding job and was actually responsible for putting the new Peter Millar shop in,” she said. But his passion is golf and he eventually left to join Greyson Clothiers, running its corporate division and working with the PGA Tour, she said.

Her third child, a daughter named Allison, started her career in fashion working for TWP and currently works for The Row.

Eventually, she said, she hopes all three of her children will work for Darien Sport Shop. “That’s the ultimate goal,” she said.

Working With Family

Much like the other successful family-owned business in Connecticut, Mitchells Stores, Darien Sport Shop has also worked with a family business consultant to write some policies and outline strategies for best practices on working with family members.

“There’s some structure within the company and what jobs you have to hold for a certain amount of time,” she said.

Gina Zangrillo said she pondered what title to give to her son Doug Reilly when he joined because his only experience was working in gift wrap during the holidays.

“I’m learning on the fly,” Reilly said. “What I’m focused on is just trying to make things as efficient as we can, get the most out of our POS system and all the different modules and resources available there. I’m looking for ways to make everybody’s lives easier, whether it’s in receiving and tracking everything that comes in and out the door, or accounting, or the way we analyze selling information for the purposes of planning and buying.

“I’m encouraging people to use AI as a tool, not a replacement, to support what we do and help us make informed decisions. How do we just become a little bit more efficient? How do we eliminate some manual work and free people’s time to think about bigger and brighter things?”

He said he’s also researching how to improve and digitize the company’s record-keeping. “That’s an area where we lack a little bit,” Reilly said, adding that today it’s not unusual for staff to run around searching for a particular customer’s order since it’s not clear what day it was brought in and who worked on it.

“There are a lot of moving parts,” his mother acknowledged. “We do a lot of business in this place — our average price point is $140 and 1,000 to 1,500 units can go out of this store on a good day. That’s between apparel and hard goods, women’s and men’s.”

Zangrillo said men’s and women’s apparel, footwear and accessories account for 90 percent of the company’s volume, with men’s just slightly bigger than women’s. The ski-leasing business is a loss leader for the store, but ultimately pays dividends.

“A family comes in in August, gets fitted for skis, they have to come back to pick up their skis, they have to come back to bring back their skis,” she said. “My father was pretty smart. If you think about a Tuesday in February where there’s a snowstorm and the schools are closed, how many people are walking into other stores that day? But here, SUVs are pulling up, running up to the ski shop, buying sleds and snow pants and snowshoes.”

She said having people walk through the women’s department with three pairs of skis under their arms when a customer is trying on a gown “just makes us what we are,” she said.

The Largest Brands

Today, Peter Millar is the largest brand in the store and is offered in both men’s and women’s. Faherty is number two and the store will be adding boys to its men’s and womenswear assortment. Johnnie-O and Vineyard Vines are also popular and all of these brands have dedicated shops within the store.

34 Heritage, which just opened a shop in the store, is becoming “a really top contender,” she added, along with Rhone, which is actually opening a store in a new development across the street. But that doesn’t faze Zangrillo.

“Our customer likes convenience,” she said. “If a guy is in the fitting room trying on pants and the salesman hands him a Rhone pant, he’s going to buy it from me. He’s not going to walk across the street. Also, we have free parking, we do free alterations — we have five tailors sewing all the time — and it’s for the life of the garment. If you lose weight, you can come in and have it tailored. We have a very lenient policy.”

The store also does well with Greyson, Rails and Kinross cashmere, the latter of which is one of its largest women’s brands. On the women’s side, Frank & Eileen is also strong, TWP continues to strengthen, and Tanya Taylor, a new addition, is also gaining fans.

She said the store draws from a large radius around Darien including Greenwich, Westport and Weston and New Canaan in Connecticut as well as Westchester in New York. Although Mitchells also has an extremely successful business in the area, she said because the stores target a different demographic, they peacefully coexist.

“We get the whole family, from birth to grandma,” she said. “Our price points are extremely different — we have home, ski, sport, and they’re much more Cucinelli. We’re serving beers and playing yard games outside the store and they’ve got a $15,000 blazer hanging. We’re so different.”

One way they are the same, however, is their passion for the business and how they service their customers and treat their employees. “They’re a family business, we’re a family business. I think you get the same feel. But I think ours is a more approachable environment.”

Maybe it has something to do with the Yeti coolers, the Maverik lacrosse sticks or the Thule racks available at Darien Sport Shop.

“I think about how smart my father was — whether it’s Saturday morning lacrosse or field hockey, dads are running in and it’s our job to entice them with something fabulous in the lobby, or that beautiful sweater,” she continued. “When mom is coming in here with her kids in tow and getting their stuff, she sees that beautiful sweater from TWP on the table.”

‘A Specialty Department Store’

Zangrillo refers to Darien Sport Shop as a “specialty department store. A guy can buy a tuxedo or a pair of Peter Millar golf slacks or soccer cleats. The beauty of the store is the convenience and the diverse products.”

Interestingly, Darien Sport Shop doesn’t sell online. “I just eliminated it,” Zangrillo said. “I don’t believe anybody in this kind of a business is making any money selling online.”

She said the company often purchases only a few pieces in a few sizes. “We buy like a boutique. In our dress department, if two customers have walked in and bought the smalls today, by the time I have them photographed and put on my website, the dress is gone. I don’t buy 700 of them. I don’t have eight stores to transfer inventory. So, for us, we just make this a happening place.”

That includes all the features now considered experiential that have become part and parcel of Darien Sport Shop over the past eight decades such as the trucks serving coffee, gelato, snow cones and grilled cheese sandwiches on Saturday mornings.  

“Families congregate here on Saturdays,” she said. “It’s unbelievable. The generational get-together is tremendous.”

For 50 years, the store has hosted the annual Christmas tree lighting in its parking lot to kick off the holiday season where Santa also makes an appearance on a fire truck. A second tree is installed in Zangrillo Park, a green space next door that the retailer added in 1998 as a gift to the town.  

And there’s the Smart Car in the parking lot that is designed to reflect the company’s commitment to sustainability but also serves as a promotional vehicle. “We’ve made a commitment to move toward ‘green,’ and are introducing new packaging, gift wrapping and more from recycled sources,” Zangrillo said. The car is also wrapped in marketing materials for the 80^th anniversary as well as the 1946 Club, the store’s newly relaunched loyalty program.

Reilly explained: “Many years ago, we used a different point-of-sale system and we had a loyalty program where you’d receive a cash reward based on how much you spent in the previous shopping month. When we moved to our current POS, the customer would get a percent of cash back on whatever they spent, but we found it didn’t really drive business. We wanted to get back to that older loyalty program structure, and figured it was a nice way to tie in the 80th anniversary, calling it the 1946 Club.”

So today, if a customer spends $200 in a month, they receive a $10 reward that would be valid for the next month, or if they spend $2,000, they get $200. “We try to be generous,” Reilly said, adding that customers also receive a $25 gift to be used in their birthday month. “We’re just trying to create a little bit more urgency to drive people into the store.”

Marking Eight Decades

To further celebrate its 80^th anniversary, Darien Sport Shop has moved away from the idea of hosting a big bash and opted instead for a series of eight events in the fall leading into the holiday season, partnering with key vendors for “fun in-store events” on weekends. The events, which start on Sept. 26, include installing a mini golf course in the parking lot, hosting an après-ski party complete with a historic chairlift and waffle treats, and a mobile coffee/cocktail bar.

“Some of the events might have nothing to do with retail, but are intended to bring people in and have some fun while they’re shopping,” Reilly said. “So we’re looking at creative ways to get people from the community involved, but also celebrate the partners and brands that have been so important to us over the years.

So after 80 years, why has Darien Sport Shop never expanded beyond its one store?

As an avid golfer, Zangrillo said she spends a lot of time in South Carolina and people there always ask her to open a store in their state. Her response?

“No, thank you. The reason I spend time in South Carolina is because I’m not here, because when I’m here, I am Gina from Darien Sport Shop, whether I’m at the grocery store, at the country club, or standing in the store. So that is my little bit of my escape.”

In addition, she believes, “It’s really hard to recreate the loyal customer base. You can find a great property, you can find a great location, but it’s our community. It’s three generations who have lived in and around Darien. They know about the lollipops that Mr. Z would hand out to keep the kids occupied when their parents and grandparents came in the store. So we still have a basket out near the front door.”

And many of the salespeople have also been there for decades, like Peter Lynch, who’s celebrating 29 years. “Customers feel like they have a person here that knows them and their family, and they know they’re going to get that personalized service.”

Although Zangrillo is still vibrant and healthy and is planning to stay with the store “until the dog kicks me out,” she has begun thinking about succession. “I feel like I’m 30 and I’m pretty energized. Business is outstanding, our team is incredible. It’s wonderful to have Doug here and I hope to see my other kids here eventually, but I don’t know what’s ahead of us. We’ll see what happens when I can’t physically do it anymore. But I don’t have to answer that question right now.”