Story

Kevin and Jenn on the beachIt took a city of 8 million to bring these 2 small town kids together. Although they both grew up in the same Upstate New York town, it wasn't until a chance meeting on a New York City subway that Kevin Chipman and Jenn Michael connected and became fast friends. Jenn on her commute home and Kevin on a visit to the city; a packed subway platform seemed the most unlikely of places for them to cross paths, yet that is exactly how these once high school acquaintances reconnected. Not having seen each other since graduation, they had a lot to catch up on.


Jenn had been busy establishing herself as an anchor in the fast paced world of fashion styling and costume design. While most post-grads were spending their time on the couch watching Saturday Night Live, MTV and Late Night w/ Jimmy Fallon, Jenn was a part of these shows. She worked with designer showrooms, high end department stores and yet-to-be-discovered boutiques to create the looks that the rest of the world was watching.


Kevin and Jenn sitting on Win Win Beachwear materialMeanwhile, Kevin had left his job as a Physical Therapist in Boston in search of more scenic views, and a change of pace from the city life. Landing in St John in the US Virgin Islands, he found the tranquil waters, white sandy beaches and beautiful year round weather to be exactly he was searching for. Although he has been living in paradise for nearly a decade, Kevin was by no means a beach bum. On the contrary, he had kept himself quite busy. An entrepreneur at heart, he had spent the last eight years nurturing his idea of an island-brewed beer (St John Brewers) and growing it into a local favorite and a nationally available brand.


As it turned out, Kevin's serene island of St. John was the perfect counterbalance to Jenn's fast-paced Manhattan existence and it wasn't long before it became her getaway of choice. During her trips the two would escape their busy lives and spend the afternoons at the beach or boating with friends. Since island tradition never has a cocktail far from hand, the two would often find their afternoon activities transitioning straight into happy hour. Sitting at the bar, wrapped in soggy towels one day, it occurred to Jenn and Kevin that surely there must be a more stylish way to dress from "beach to bar". Jenn knew of the perfect clothing compliment for this lifestyle, but also knew they were nearly impossible to find. Something that has the softness and absorbency of a towel but that also has the fun, eye-catching factor of a Hawaiian shirt. Eureka! The idea for Win Win was born — a 1950's inspired cabana set. Pairing Kevin's business background with Jenn's fashion sense could be nothing less than a Win Win situation so it wasn't long before their idea started to take shape.


Win Win Beachwear is available in mens' cabana sets (Win Win) and baby (Lil' Win) sizes. Our newly launched women's collection (Lady Wins), has already made a splash with our Mod Dress and Swing Coats being featured on ModCloth.com. With all of our pieces consisting of plush terry cloth AND stylish patterns and prints, our goal is to bring fashion meets function to a beach, bar or pool near you!

Browse our Collection to Get Your Win Win