Long before our founder, Susan Hassett, began a love affair with Cocktail Sneakers, there was a special someone who believed she could turn her dreams into a reality. The story of Cocktail Sneakers really began with the story of Susan and her amazing husband of thirty-five years, John.

This is your 38th Valentine’s Day spent together with your husband. How did you meet John?

It was one summer in Boston when we were young, single, and carefree. I had a great group of friends and we’d always go out together after work and on weekends. We were out one night when my friend, Jack, introduced me to his friend, John.

Was it love at first sight?

It didn’t cross my mind at the time that we would be anything more than casual acquaintances. In fact, I didn’t even remember his name! I ran into him again two or three more times but it wasn't until I was at a small Sunday afternoon party in Marblehead when I mentioned to Jack that I kept bumping into his friend . . . what’s his name again? And just at that very moment, who would round the corner but John!

We had a fun afternoon and when I got to work the next day—late as usual—there were three messages waiting for me. John wanted to meet for lunch that day.

So, you fell in love over sandwiches?

Maybe, but I wasn't really looking for anything so I didn't even think about it; we were just two friends meeting for lunch on our break. It was time to order and I really wanted a glass of milk but I didn’t want to look like a dork. But then John ordered a glass of milk. I took notice—we quite possibly could have been the only two luncheon milk drinkers in all of downtown Boston! This was my first “sign.” Then, he asked me out on our first real date . . . that night! 

Did you change your outfit?

No, I had on a summer dress and sandals and didn’t have time to change. I must have been feeling something in my heart by then because I remember exactly what John was wearing, down to the brown penny loafers he was wearing without socks. We were heading to Cambridge to see a jazz band when the weather flipped; it went from a hot summer day to a cold fall night just like that. We were freezing! We were both young and broke. John had started his own company and was on a shoestring budget, but he bought us both these matching wool sweaters that night—which we still have although John shrunk them in the dryer. That was a Monday, and we have been together ever since!

You joke that John is the only man on your all-female team. Tell us how he’s involved.

John isn’t directly involved but he’s more of a benefic force in my life. John has always been an entrepreneur. He is such a positive person and he sees all the possibilities and the potential in life and in me. When I had my doubts about starting a business, it was John who gave me the nudge. He bought the domain name for me one night when I was on the fence, thinking of reasons why I couldn’t or shouldn’t. He believes in Cocktail Sneakers—the concept, my vision for the brand, and most of all, he believes in me.

Any special plans this Valentine's Day?

I’m very sentimental and I’ve often felt that the big gestures aren’t nearly as meaningful as the smaller ones . . . a single flower, a hand-written poem (which John has written for me before). When it comes to Valentine's Day, I don’t need much—just a warm wool sweater (that hasn't been shrunken), a cocktail (or glass of milk) and John by my side.

We started chasing our dreams years ago, and we’ll keep chasing the sun together!