How To Nail Smart Casual Like Roger Sterling

Let the best-dressed Mad Man be your guide this summer

Don Draper may have stolen all the headlines since Mad Men first aired back in 2007 but it’s always really been about Roger Stirling. Admittedly DD’s pulling power would have its moments but when it comes down to the nitty-gritty, who would you rather be? The monotone and angst-ridden one or funny, charming and likable?

To top it all, he’s been better-dressed than Don from day one. It’s Stirling's suit, shirt and tie combinations that first gave Mad Men style its name and the latest series is no different. While Don’s conservative approach has remained largely unchanged through seven seasons, Stirling’s dress has recently benefited from a little late Sixties Californian colour.

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The real stand-out look from the latest run is the Stirling broken-up suit, combining double-breasted jacket, white shirt and contrast colour patterned trousers. It’s a combination that’ll work as well today as it might have done back in 1969.

Here’s how to recreate it right now:

The Jacket

This double-breasted blazer is an almost perfect match for Stirling’s own, right down to the white buttons and wider pique collars. £495, Kent & Curwen

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The Trousers


While your jacket plays the straight man, let the trousers do the shouting. These plaid cotton numbers are authentically loud right down to the pink accent that will play off against the navy blue. £95, Ted Baker

The Tie 

Pull it altogether with a tie that bridges the gap between loud trousers and dark jacket. The woven texture of this wine-coloured Grenadine fits the brief perfectly. £95, by Drake's London