Don Draper (aka Walt Whitman), faultlessly played by Jon Hamm, was a style icon from the moment the show first aired. His magnetic charm belies a searing darkness which is the show’s narrative centre.
Buoyed by his matinee idol looks, fitting so well with the 1950s and 60s aesthetic, Draper’s signature style is classic Brooks Brothers. He showcases minimally structured suits in shades of blue and grey. Single vent is the norm although doubles are seen. Waist suppression is limited which leads his suiting to approach boxiness, although for a man whose frame is essentially composed of rectangles, some boxiness is to be expected (and forgiven). His ties are extraordinarily thin and tied in a simple knot, a look that breaks from conventional wisdom and leads to an imbalanced portrait due to his exceptionally large head. His huge head has brought him acclaim and fortune, however, so who am I to judge?
Greatest style moment: Season 3, Episode 8, Souvenir. In a playful and sexy scene, Draper joins his wife for an alfresco dinner in Rome. He very nearly outshines her in a pale blue silk sports jacket, simple white shirt, champagne ‘neat paisley’ tie and black chinos. The shimmer of the jacket and tie, whose shade matches his skin tone while other elements of the ensemble are muted, makes this outfit sing. This scene is the style pinnacle for both characters and the highlight of their onscreen relationship.
Roger Sterling, a man of wealth and taste, is undoubtedly the true rake of the show. Despite his advanced years, his womanising exceeds Draper’s, and his immaturity is boundless. Many of the most joyful moments in the series concern the pair’s friendship and badinage.
The only thing sharper than Sterling’s wit is his tailoring. His signature look is the three piece suit. A variety of colours are seen but silvery grey, in symphonic harmony with his mantle, shines out. Sterling’s bright white hair is the lynchpin of his style. In everything he wears, something, be it tie, pocket square or pin, will link the outfit to his mane and the results are magnificent. Sterling turns pattern matching into high art; checks, stripes, paisleys and polka dots play together like old friends. As for fit, there is only one word in Sterling’s consumer vocabulary: bespoke.
Greatest style moment: Season 7, The moustache. A masterstroke by the show runners, the simple addition of the moustache hails the show’s progression from 60s to 70s without the need for unsightly prosthetics. Sophistication and whimsy are added to a man already well stocked in both.
If you can do as good a job as these two, do remember
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