Recently, Jamaican-Canadian designer Kirk Pickersgill celebrated his 20th year in business, and the milestone anniversary had him pondering the future while bringing his new resort collection to life. “I’m calling this collection ‘Next,’ because people keep asking me what’s next,” says Pickersgill. “My answer to that is, I’m just going to keep doing what I’ve been doing.”

Known for his cocktail dresses and elegant occasion gowns, Pickersgill did not mean this as a way of staying stagnant—rather, he wanted to double down on what he does best, and find a fresh new way to interpret what his customers expect of him. For resort, he was particularly inspired by the idea of Sunday Best—creating fancy-fun clothes that reflect the designs he saw at Sunday mass growing up. “For us, Sundays were always about going to church,” says Pickersgill. “My mother used to dress my sisters like twins, and I would be dressed as the boy version of them.”

Pickersgill particularly recalled all of the vibrant, upbeat colors he would see amongst the church crowd, and wanted to bring that pastel palette into his new assortment. For daytime, he created a minty-green maxi skirt in a floral-appliquéd cotton, which felt chic against his crisp white dress shirt with slightly puffed sleeves. A silky-butter yellow tunic featured a high neckline and billowing hemline, which had such a beautiful drape that it doesn’t really require wearing much else. (His most unexpected daytime offering, meanwhile, was a light-blue sequined pair of trousers that resembled a pair of classic but jeans—paired with a graphic tee that simply read “Greta,” an unnecessary dose of logomania.)

The sugary hues continued on into evening, an area in which Greta Constantine always shines. His soft-pink, floor-length caftan was covered in a gauzy sequin. For those who prefer more tonal or discrete dressing, his black strapless evening gown came with ruffle detailing, as well as a built-in white chiffon scarf attached at the neck: It could be draped to one shoulders, or slung in front of the neck to cascade at each side of the back. Pickersgill always wants to give his women options, from subdued to over-the-top. “I’d love to see someone wear this to church—now that would be fascinating,” says Pickersgill.