Born and raised in Connecticut, James Coviello moved to New York City in 1984, and attended Parsons School of Design. He resides in Brooklyn Heights. He enjoys spending weekends and summers away from the city renovating, decorating, and gardening at his nineteenth-century country home in New York's Hudson River Valley.

In a twist to the traditional fashion career, Coviello started out as a milliner in 1987. His unique hat designs captivated the fashion world, and were soon featured on the runways of fashion luminaries including Anna Sui, Calvin Klein, Geoffrey Beene and Oscar de la Renta. High-end retailers including Barneys New York, Bergdorf Goodman, Henri Bendel and Neiman Marcus sold the hats throughout the 1990s, featuring them in their creative window displays. Today, in a tribute to these beginnings, Coviello's ready-to-wear label features a monkey in a top hat surrounded by even more hats.

In 1991, Coviello designed hats as well as knitwear for Anna Sui establishing James Coviello for Anna Sui the following year. The creative collaboration between these designers flourishes, and he continues to design for her runway shows each season.