The Value of a Genuine Relationship

Over the last ten years, Caroline Olson has wanted to expand both her family and her impact on the local community. Driven by an old-fashioned New England work ethic and a refusal not to reach her goals, Caroline’s plans have become her everyday passion – but it has not been easy, and it has largely been by managing two major events at the same time. 

Olson is the founder and owner of Pearls & Plaid, a one-of-a-kind boutique that stands out even amongst the highly creative shops of the Connecticut shoreline. Since her high school job in a small Deep River clothing store, “I knew I wanted to have my own business, but I didn’t know what that looked like.”

As if opening a business at 22 years old was not challenging enough, Caroline was going through another major life change: She was three months pregnant. Caroline and her husband, Alex, welcomed baby Teddy to the world, and the Pearls & Plaid business earned a modest but loyal following over the next four years.

In 2018, Caroline moved the store to a bigger location – this time, when she was eight months pregnant with her son, Harry. Like many business owners, the 2020 pandemic posed a severe threat to all of her plans, but Caroline did not flinch. In fact, she doubled down again and opened Post Road Supply – a sibling boutique of Pearls & Plaid focused on men’s clothing. “I always dreamed of being on a main street,” she says, making that reality in 2021 when she bought her business’ forever home on Main Street in Old Saybrook.

“They have done small banking and big banking for me and my family – everything from $25,000 loans to mortgages.” (She is not kidding about the banking done for her family; Caroline’s husband owns JRI Concrete in Clinton and moved his business accounts to Essex after “feeling like the previous bank prioritized policy over people;” Teddy and Harry both have accounts with the Bank, and Teddy loves walking into the Bank’s Saybrook branch with his earnings from the Ted’s Toys concession machine located in the front of the Pearls & Plaid store.)  

2023 was another double whammy: Caroline opened a second store, adding a Niantic location to the Old Saybrook flagship, and also welcomed her third son, Winston.

“They have been a helping hand through all different stages of this business and just my life personally,” she says. “Banking and the financial aspect of things can be really confusing, scary even. Not only does the Essex Bank team help me understand everything, they truly back what I believe in.”

She is very complimentary about the Bank technology that provides a backbone to her business, especially during times when Caroline is traveling out of state on buying trips. “I can be anywhere – Atlanta, New York, another city – and the mobile app keeps me updated at all times. Their online banking is sophisticated in terms of services, but very easy to use. And if I have questions, the Bank has actual people who can answer them.”

So, does Caroline have plans to do more “doubling down?” For now, she is content to pour everything she has into her boys and her business. (That said, she and Alex are finishing up the construction of a brand new house in Deep River – yet another major project that caused her more than once to look in the mirror and ask herself why she cannot “just slow down.”) 

Truth be told, underneath all of her ambition lies an important characteristic that drives her, and that has kept Caroline coming back over many years to the Essex Bank team.