Wilson, born in 1956, graduated with a Bachelor of Arts in economics from the University of Calgary in 1980. He has five sons, two from his first marriage, to Nancy, and is married to Shannon Wilson, one of the original designers of Lululemon and co-founder of Kit and Ace, along with his son JJ Wilson. They reside in Vancouver, BC.

In 1979, Wilson founded his first Retail apparel company, Westbeach Snowboard Ltd., which sold apparel targeted at the surf, skate, and snowboard markets. Wilson went on to sell Westbeach in 1997 and founded Lululemon Athletica Inc. in 1998. As of 2016, his personal and Business interests are maintained through Hold It All Inc.

In 2004 Ernst & Young named Wilson its Canadian Entrepreneur of the Year for Innovation and Marketing. As of 2012, Forbes ranked Wilson the 10th-wealthiest Canadian and 401st in the world, with an estimated net worth as of March  2013 of $2.9 billion.

Wilson served as CEO of Lululemon until 2005, when he sold a 48% minority stake in the company to private equity firms Advent International and Highland Capital Partners. In 2007 an IPO was offered by Lululemon Athletica Inc. on Canadian and US exchanges. In January 2012, Wilson retired from his executive post as chief innovation and branding officer, but remained chairman of the board of Directors. In December 2013, he stepped down from his role as non-executive chairman.

In 2007, Wilson and his wife, Shannon Wilson, launched imagine1day, a charity dedicated to improving education conditions in Ethiopia. The organization's goal is for all Ethiopians to have access to quality education free of foreign aid funding by 2030. As of June 2016, imagine1day had 487 partner schools, 35 of them built from the ground up by its team. Also, 1,130 school clubs had been created, with half run by girls. 66,420 books, 180 science kits, and 160 Sports sets had been provided to students. Imagine1day estimates that over 252,000 lives are transformed annually through its education and training.

On November 18, 2013, Wilson was the subject of the Stephen Colbert show's segment "Alpha Dog of the Week"; Colbert sarcastically criticized Wilson for his views on the influence of birth control and for having said that some women's bodies "just actually don't work" for his company's pants.

Chip and Shannon Wilson are leading sponsors of the annual Child Run. The Child Run is the largest family fun run in Vancouver, with a 5 km for runners and walkers on a scenic route through Queen Elizabeth Park and a 1 km fun run, followed by a carnival celebration. Proceeds support British Columbia's Children's Hospital and its fight against childhood cancer. In 2014, the run had over 6,000 participants and raised over $1 million.

Wilson appeared in a CBS interview in 2015 where he apologized for past statements regarding the Lululemon yoga pant scandal, saying, "I'm responsible for what comes out of my mouth. And if that's what was interpreted then I fully apologize. Yeah. I'm sorry."

In June 2016, Wilson published an open letter to shareholders of Lululemon stating that Lululemon had "lost its way" and given up market share to Nike and Under Armour, after he was denied the opportunity to speak at the company's annual meetings.