The activity, devised by creative agency Exposure, marks the footwear brand's 50th anniversary. It aims to celebrate Dr Martens' rich association with fashion, culture and music during its half-century.
As part of the campaign 10 contemporary bands have been invited to record cover versions of classic tracks.
Filmmakers, including Ace Norton, and fashion photographer Rankin, have also been commissioned to shoot music videos for the songs.
Three tracks and videos will be available for download exclusively from the Dr Martens website from next week. The remaining seven will be released in stages during the rest of the year.
The site, created by agency Love, will also feature behind-the-scenes footage and photographs of the artists, along with documentaries about the brand's history.
The tracks include 'Ever Fallen in Love' by the Buzzcocks, which will be covered by Noisettes, the Raveonettes' version of 'I Wanna Be Adored' by the Stone Roses and the Pogues' 'Dirty Old Town' performed by Black Rebel Motorcycle Club.
In the past, Dr Martens has released album compilations and sponsored music festivals. It has now decided to focus its efforts online to engage with younger consumers, while continuing to communicate with "die-hard" brand loyalists.
The brand also plans to release limited editions of its classic 1460 and 1461 style boots and shoes.The activity will be rolled out across social networking and music sites, and press ads will appear in the May issues of national magazines.
A spokesman for the brand said: "Dr Martens has been linked with music for five decades, various youth subcultures, and the musicians they associated with, adopted the Dr Martens boot as part of their rebellious uniform."
In 2007, the brand was embroiled in controversy after it ran a print campaign featuring dead rock stars, including Nirvana front man Kurt Cobain and Sex Pistols bassist Sid Vicious, wearing the footwear in heaven.
The agency behind the campaign, Saatchi & Saatchi, was then dropped by Dr Martens because the brand had not commissioned the activity.
The previous year Dr Martens had attempted to gain a following online by creating its own social network. However, this was later shut down.
DM timeline
1960: Dr Martens began pro-ducing boots in the UK on 1 April. The product took its 1460 name from this date.
60s: DM boots became the footwear of choice for skinheads.
1984: Products went on sale in the US.
1992: Dr Martens clothing line was established.
1998: Dr Martens signed up as shirt sponsor of West Ham United FC.
2000: Launched compilation album in the UK. Acts included The Sex Pistols, Iggy Pop, The Clash and Morrissey.
2005: Products distributed in more than 70 countries.
Source: Dr Martens