Family Dynasties in Fairfield County

by Jaime Willie

Connecticut isn’t only haute in the summer. These Fairfield-county businesses keep fashion in the family

Fairfield County is a place where customers are friends and family comes first. The family-owned business came decades before the consumer-driven market and has lasted in few places. And although some would argue small family businesses are far and few, Connecticut has bragging rights to some of the most successful.

Who would’ve thought CT would be credited with big name fashion icons and empires including, Tommy Hilfiger, Mitchell’s, Windsong, and True Blue in New Canaan—all of which have either founded or found themselves in Connecticut and all which are family-owned fashion businesses. With mass production and merging companies on the rise, it’s no surprise that these family-owned businesses, who have what it takes to stick around, are turning heads and making sales. So what is it about Connecticut that makes these successful businesses want to stay in the family and stay in the area?

David Sweedler, president of Windsong, and Bob Mitchell, co-president of Mitchell’s and Richard’s, both started their careers in Connecticut and understand why family-businesses plan to stay just as they do.

Named after a ’57 custom fishing boat, Windsong has been in the family since 1993 when it was established by Sweedler’s father, Joseph Sweedler. Joseph has been in the fashion industry his whole life, and although he worked in New York City for most of his career, he eventually started his own business in Westport. Sweedler says his father kept growing the business in Westport and will continue to do so. “Ct is a wonderful place to do business because of the proximity to NYC. It is the hub of most industries in the world so it was a natural choice,” says Sweedler.

Another family-owned business plans on staying in Ct as well. The Mitchell’s store in Westport has remained a stationed fashion house since 1958. Tired of the daily commute to New York City, Edwin (Ed) and Norma Mitchell chose an 800 sq. ft. building to implement the very first Mitchell’s store. Since the store opening, the business has remained in the family—today there are 7 members of the second generation and 3 members of the first. The company has grown 10xs since 1991 and acquired Richard’s in Greenwich and most recently Marsh’s in Long Island.

Mitchell says, “Since day one I tried to be community serviced. Our motto has always been ‘Once a customer, always a friend’.” 

If there is one thing family-owned businesses are known for, it’s their invaluable customer service. Sweedler says, “We’ve really stayed in Connecticut for the people. Westport is a wonderful place, the people are friendly, and we know almost everyone and I would consider them all our friends.”

There is a certain customer service that shoppers get when walking into a family-owned business that assures them that they will be taken care of and remembered. It’s a place where everyone knows your name. It’s the familiarity customers might not be able to find at a larger consumer department store.

Beyond the friendliness and specialized (individualized) customer service, there also needs to be a strategy within the company that helps guarantee the success that is so hard to achieve in small businesses. Like any company, there are always going to be internal problems, but it’s hard to imagine the situation being any easier for companies that are made up of families. Mitchell says, “We’ve had a consultant since 1985 that helps facilitate issues. But we work really hard and we work very well together.”

Sweedler says, “The pros and cons are the same; you work with family. You’ve got built-in day care when you need it and there is no greater feeling and accomplishment in business than succeeding with your family members. But on the other hand, we argue because we are all very opinionated so that makes for interesting board meetings.” Sweedler continues, “At the end of the day, we’re family. We makeup and move on to the next goal.”

Even as the companies continue to grow and prove successful, Windsong and Mitchell’s have no plans for leaving Connecticut. As in terms of the future, Sweedler says, “We recently purchased the Calvin Klein Golf license for worldwide distribution. But the company will always stay in the family.” It will also remain a Connecticut fashion powerhouse for a long time.

One can only assume success is brought on by a cycle—better family-oriented customer service within a shorter commute leads to more time with the family, which in turn leads to better family-oriented customer service.

Mitchell says, “We look at having a family business as a huge positive. We always treat it as a business first but it’s an added bonus that the people you work with are family. But above all, there needs to be balance of family and non-family members—it’s the key to a successful business.”