This season, Nicky Zimmermann began with a historical event, rather than a feeling—the 1983 America’s Cup. (For those interested in a full account of the underdog Australian sailing team dethroning the American champions, a formative memory for any Australian of a certain age, Zimmermann recommends the Netflix documentary, Untold: The Race of the Century.) “The story resonates not just from my childhood, but as something that is a really feel-good story for any generation,” the Sydney-based designer said.

For quite a tangible starting point, the inspiration manifested less literally than one might have thought. Resort collections and sailboats don’t have to directly equate to a boatneck striped T-shirt and topsiders, and it’s better when they don’t. A digitally printed dress made from silk georgette layered over a silk satin organza took on a more ephemeral interpretation instead. “I think the beautiful imagery of the sailboats also resonated because of the movement, and I love to be able to represent that in clothing, through the shapes of the sails and those kinds of details,” Zimmermann explained. A drop waist dress and colored shearlings evoked the yacht-club good life.

Elsewhere, a vacation ready striped cotton poplin frock sat alongside more formal, but not frilly, eveningwear. The balance brought a new look to Zimmermann, which is known for its ruffled creations. That balance is necessary, especially as designers grapple with designing for the increasingly vague category of a resort season. “We have a massive clientele in Florida that this collection is incredibly important for,” Zimmermann said. “But then they also are in New York, and they’ll want the colored shearling, and they’ll want the long lace dress. For me, it really makes sense to be able to try and answer those questions.”