Dean and Dan Caten were born in 1964 in Toronto, Ontario and grew up in Willowdale. They have seven older siblings. Their father is from Casalvieri, a small town in Ciociaria, Lazio, Italy. In 1983, they moved to New York to study fashion at Parsons School of Design, but stayed for only one semester before returning to Toronto.

Finding a financial backer in 1986, they launched their first signature womenswear collection, DEanDAN. By 1988 they had signed on to label Ports International (currently Ports 1961) as creative directors. At the same time, the Catens designed for their lower-end, leisure brand, Tabi International. In 1991, the brothers moved to Milan, Italy where they worked as designers for the house of Gianni Versace, and denim brand Diesel, the latter of which funded and launched their namesake brand. They debuted their men’s collection in 1994, and in 2003, they launched a women’s collection and a men’s underwear collection.

A runway show in 2005 ended with Christina Aguilera stripping male models of their clothes. In September 2007, the Dsquared² fashion show in Milan featured Rihanna entering the stage in an American muscle car, followed by a runway walk. In January 2010, the Dsquared² Autumn/Winter 2010 menswear show in Milan featured Bill Kaulitz descending from the ceiling in a caged elevator à la Rocky Horror Picture Show. Bill Kaulitz opened and closed the Dsquared² Autumn/Winter 2010 menswear show in Milan.

In 2006, the brothers were selected to design the new official uniforms for football team Juventus. In March 2008, the Catens signed an agreement to design sunglasses with Marcolin, an Italian sunglasses and eyeglasses manufacturer.

In June 2007, the first Dsquared² flagship was opened in Milan’s fashion district. Stores also opened in St. Moritz, Athens, Mykonos, Capri, Istanbul, Kiev, Cannes, Singapore, Paris, Nicosia and Hong Kong. In March 2015, Dsquared² opened their first flagship store in London. This is the first stage of their major store redesign programme that will continue into the US at the end of 2015. More recent Dsquared² stores openings have included Miami, Doha, Los Angeles, New York, Baku, Rome, Istanbul and Madrid.

In 2013, the Dsquared² brand had a brand turnover of about €200 million. The brand generates most of its revenues through licensing deals.