Jeff Casler, Founder & CEO

When asked what brought him to the consignment business, Second Time Around CEO Jeff Casler has a simple answer — he was born into it! Jeff’s mother, Dottie Casler, is the founder of Second Time Around, a renegade in her time who opened the first consignment store in Newton Highlands, MA in 1973. Long before Jeff took the reigns of the company, Dottie was Second Time Around’s matriarch, bringing her small town’s shoppers the stylish clothes they craved, and laying the foundation for what STA has grown into today. From a young age, Jeff was a regular helper at the store, and he soon became fascinated by the fast pace of retail and his mother’s knack for knowing each client by name, size, and style.

After years spent immersed in the family company, Jeff left to study business at the University of Massachusetts at Amherst. He decided to pursue a career in accounting, but crunching numbers proved a far cry from the excitement of the retail and fashion industry. In the end, it became clear that Jeff’s passion lied in a career that allowed him to exercise his creative energies and his savvy business sense. Soon enough, that passion led Jeff back to Second Time Around. Armed with deeply rooted confidence in the company’s potential, he set out to grow Second Time Around into something bigger than the already thriving store his mother had created.

For the next 20 years, Jeff worked diligently at building the brand, branching out into new markets and watching the customer base grow at every turn. Success in the consignment industry can be elusive, but Jeff’s sharp business sense and his eye for style were a worthy match for the challenge. Cities that once seemed like far-off possibilities — New York, D.C., and Chicago — became home to new Second Time Around stores, and what had started as a small suburban shop blossomed into a nationally recognized leader in the consignment industry.

The passionate and loyal following that Second Time Around has attracted is a source of great pride for Jeff. From day one, he recognized that such astounding growth would not be possible without a talented and dedicated staff, and indeed, Second Time Around’s marvelous employees have been an integral part of the company’s success. Jeff is a champion of employee training, retention, and advancement, and under his guidance, the company works contine to nurture and foster employees’ strengths and ensure their success within the company. The staff’s incredible devotion to customer service and passion for style, along with our loyal and fashionable consignors and customers, has made Second Time Around what it is today — a brand synonymous with chic, stylish, and trendsetting clothes at affordable prices.

Jeff Casler lives in West of Boston with his wife, two children, and a puppy named Percy. On any given workday, you’ll find Jeff casual, comfortable, and professional in a North Face pullover, J. Crew shirt, and Adidas sneakers, with Percy by his side.

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