Hemingway started his fashion career by selling items from his wardrobe, and that of his childhood sweetheart (now wife) Gerardine, in
Camden Market. They proved successful, and by the end of the year they had 16 stalls at the market, with shipments of second-hand clothing and footwear brought in from all over the world. By 1983, they had opened a shop in
Kensington, London, selling Gerardine's self-made clothes. That same year, the first Red or Dead collection was also created, inspired by Russian peasant clothing. It was well received and they obtained a large order from the US department store
Macy's. Red or Dead stores began to sell
Dr. Martens work-wear shoes as a fashion item, and thus began a range of fashion shoes within the stores. In 1998 Wayne and Gerardine Hemingway sold the Red or Dead company to
Pentland Group a privately held, global brand management company. The sale financed Gerardine's design of their house in
Chichester, West Sussex. The house cost around £330,000 to build and furnish (in 2005). In 1999 they set up 'HemingwayDesign', which specialises in affordable and social design. The highest profile project Homes. the
Staiths South Bank, an 800 property mass market housing project on
Tyneside for
Taylor Wimpey Homes Award has won a series of high-profile awards, including the 2005 Housing Design Award for best large project and Building Magazine's "Best Housing-Led Regeneration Project" and the highest rating of any large-scale scheme in a recent
CABE audit. He designed the
Pure Bug digital radio receiver. Hemingway has designed beachpods in
Boscombe for rent and sale, which raised over £1 million for the local authority. Hemingway's team organised a cultural event in August 2010, the Vintage Festival. In 2011, the festival took place at
Southbank Centre in London, as part of the 60th anniversary of the
Festival of Britain (held originally in 1951), and again in 2012. In 2013, the Vintage Festival took place in
Glasgow and
Morecambe. Hemingway said A Vintage New Year was held at Southbank Centre in 2013. October 2013 saw the launch of Vintage presents A Classic Car Boot Sale. In 2012, Wayne, Gerardine, and the HemingwayDesign team were appointed as designers of the historic and disused
Dreamland site in
Margate. This included the transformation and branding of the £10m heritage
theme park. In 2012, Hemingway received an honorary degree (Doctor of Arts) from
Leeds Metropolitan University. In 2014, Hemingway's company introduced a new London Underground staff uniform, initially trialled at several stations and train depots before being introduced company-wide in 2015. In the same year, it was announced he was to become patron of
The Unite Foundation, a charity providing free university accommodation to young people in the UK from challenging backgrounds. ==Family==