The print initiative, by Grey London, is the first to be produced by the agency since it recaptured the account in May.
The campaign, which breaks this week, is intended not only to sustain the brand's existing customer base, but to tap into a younger market.
It aims to extend Ben Sherman's reputation beyond shirts by promoting a wider variety of fashions including women's wear, denim, footwear and formal wear.
The message will be delivered in a series of ten print executions underlining the label's contemporary and multicultural popularity by twinning places or towns in the UK with their namesakes in other countries.
These include Soho in London with SoHo in New York, as well as two famous Oxford Streets, one in London and the other in Sydney.
Written by Adam Chiappe, art directed by Matt Saunby and photographed by Barnaby Roper, the ads will break initially in Maxim in the UK and will also appear in the US and Canada over the next five months. Naked Ambition is handling media strategy.
Andy Rigg, the Ben Sherman marketing director, said: "We're enjoying significant growth both on our home turf and beyond. We now have all the pieces in hand to enable the brand to fulfil its potential as the ultimate British lifestyle brand."
Dylan Williams, Grey London's executive planning director, commented: "When a brand has as colourful a past as Ben Sherman, the temptation is to go retro. But 'twin towns' allows us to celebrate the brand's role in today's global multicultural youth scene rather than simply give a history lesson on the British teenager."