The style lessons to learn from Mad Men’s Don Draper

Whether it’s adding patterns and prints to your suiting, or investing in a signature pair of sunglasses, here’s how to dress like the all-American ad man…

Don Draper may be the archetypal, all-American ad man — but his assumed surname is most-associated with another profession. Derived from the French ‘drapier’, Don’s family name has its origins in the textile and clothing industry. But that’s no wonder, as — during the seven slick seasons of AMC’s seminal drama series — Jon Hamm’s sharply-realised role was one of the best-dressed characters on the box.

Inspired by real-life advertising executives Draper Daniels and Bill Backer, Mad Men’s Draper surfed the styles of mid-century America — donning everything from double-denim to felted fedoras during the series’ fictional spin through the sixties. Here, we’ve slipped back through the show’s seven seasons, picked out the ad man’s most influential looks, and laid out the lessons you should learn from them…

Add a striped tie into your tailoring rotation

Don Draper’s tailoring didn’t change the world — at least not to the extent of his advertising campaigns. He tended to wear a staple American suit; slightly boxy, soft and thick in the chest and with a whisper of a taper at the waist. It was a style was popularised throughout the mid-century US by Brooks Brothers and Ralph Lauren and, today, it would look a little shapeless. But Draper’s ties? That’s a striped style worth knotting up yourself.

Slim, diagonally-patterned and subtly blue, we’d turn to New & Lingwood if you’re looking to emulate Draper’s cool — with this grenadine option created with a handsome open weave. Alternatively, if you’re going a little bolder, try Drake’s. There’s a whole range of block-striped ties on offer from the brand, but this hand-rolled blue option is the most Mad Men option. 

The style lessons to learn from Mad Men’s Don Draper

New & Lingwood Fine Stripe Grenadine Tie

£95

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The style lessons to learn from Mad Men’s Don Draper

Emma Willis Superior White Shirt

£240

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The style lessons to learn from Mad Men’s Don Draper

Drake’s Shantung Silk Grenadine Tie

£145

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Check out Draper's patterned blazers, and buy one yourself

Though Don Draper’s suits may have been serviceable — if not impactful — the ad man’s blazers turned even more heads than his billboards. Bold, colourful and invariably checked, the sixties-style may seem garish in the cold light of the 21st Century, but we’d still suggest giving the gaudiness a chance.

Ralph Lauren’s Italian-crafted, half-canvassed jacket puts a modern spin on classic preppy style. Hackett has followed fashionable suit, with a windowpane check jacket in a rick dark green. And Paul Smith has captured the elegant essence of Draper’s blazers thanks to a set-in lapel and soft-shoulder construction.

The style lessons to learn from Mad Men’s Don Draper

Ralph Lauren Plaid Silk-Blend Jacket

£520

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The style lessons to learn from Mad Men’s Don Draper

Hackett Windowpane Check Blazer

£475

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The style lessons to learn from Mad Men’s Don Draper

Paul Smith Check Wool-Silk Blazer

£750

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Scope out a pair of signature, statement sunglasses

Whether he was wearing a pair of square-framed Randolph Engineering aviators, or Ray-Ban’s gold, rectangular Olympian I Deluxes, Don Draper knew how to style his shades. He may have been on a Hawaiian beach, or behind the wheel of his 1964 Chrysler Imperial convertible, but the ad man’s gleaming, wire-framed sunglasses were one of his statement, signature pieces for all seven seasons of the drama.

If you’re looking to emulate Draper’s frames, we’d first turn to Monc, whose ‘Lymington’ style was inspired by retro filmmakers. Similarly, TBD Eyewear’s ‘Vicuna’ sunglasses give off a 24-carat glint — but boast brown lenses more tobacco-tinted than the ad man’s ‘Old Gold’ cigarettes. Or, for a little more detail, Cubitts’ ‘Calshot Fold’ frames feature a filigree rim and mineral glass lenses.

The style lessons to learn from Mad Men’s Don Draper

Monc ‘Lymington’ Sunglasses

£230

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The style lessons to learn from Mad Men’s Don Draper

TBD Eyewear ‘Vicuna’ Sunglasses

£250

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The style lessons to learn from Mad Men’s Don Draper

Cubitts ‘Calshot Fold’ Sunglasses

£125

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Find an overcoat to complement your tailoring

Though Draper’s colossal whiskey consumption — the maverick ad man favoured the spirited, slightly spicy ‘Canadian Club’ — would have seen him through even the most bitter winter. And yet, Jon Hamm’s iconic character buttoned up a bevy of well-cut overcoats during his time at Sterling Cooper.

In his earlier days, Draper opted for darker colours. Versatile and practical, both Sunspel and Loro Piana have very similar styles at very different price points, that will both happily and handsomely complement every suit hanging in your wardrobe. Later in the series’ run, the coats went more camel-coloured; a light brown look rendered in warm wool by Paul Smith. 

The style lessons to learn from Mad Men’s Don Draper

Sunspel Navy Cashmere Overcoat

£650

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The style lessons to learn from Mad Men’s Don Draper

Paul Smith Single-Breasted Coat

£450

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The style lessons to learn from Mad Men’s Don Draper

Loro Piana ‘Sartorial’ Coat

£4420

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Keep your eveningwear ensembles traditionally-tailored

In the first season of Mad Men, we get a glimpse of Don Draper’s earliest eveningwear ensemble. Dabbling with black tie at New Year 1956, the ad man pulled on a blue silk plaid dinner jacket over his crisp white shirt and black bow tie. Thankfully, in subsequent seasons, this lurid style doesn’t get another look-in. And, aside from season two — in which Draper toyed with an ivory jacket — he kept things largely classic.

A staple of his formalwear was a series of bold black dress studs, such as these Aspinal of London accessories. His bow ties were always self-tied, as spotted after Draper attended the Advertising Club of New York’s annual awards banquet in season six (try Eton Shirts for this). And his shirts, although never pleated on screen, had all of the pomp and character of Turnbull & Asser’s white dress shirt. 

The style lessons to learn from Mad Men’s Don Draper

Eton Shirts Black Bow Tie

£80

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The style lessons to learn from Mad Men’s Don Draper

Turnbull & Asser Pleated White Cotton Dress Shirt

£300

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The style lessons to learn from Mad Men’s Don Draper


Aspinal of London Black Mother-of-Pearl Dress Studs

£220

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Choose a restrained, but well-made wristwatch

Speaking of dinner jackets, one of Don Draper’s first watches in Mad Men was a Jaeger-LeCoultre ‘Memovox’ with an idiosyncratic black-and-white dial, dubbed ‘tuxedo’. But that wasn’t the ad man’s best model from the Swiss watchmaker. As, from the second season, he opted for a ‘Reverso Classic’, one of the most iconic watches ever made.

Elsewhere throughout the acclaimed show’s run, Draper went for a more sporty, trimmer timepiece. In stainless steel, and boasting a jet black dial, the Rolex ‘Explorer’ made a shiny-buckled appearance in the fourth season, and the final three seasons had their times told by Draper’s Omega ‘Seamaster DeVille’ — a plain proposition, but one with beautiful baton hands and an elegant crosshair dial. 

The style lessons to learn from Mad Men’s Don Draper

Jaeger-LeCoultre Reverso Classic

£5650

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The style lessons to learn from Mad Men’s Don Draper

Omega De Ville ‘Prestige’ Chronometer

£4200

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Enjoy your downtime in some natty knitwear

From the moment we were introduced to the man, it was clear that Don Draper was no soft touch. And yet, as the seasons unravelled, the ad man’s penchant for knitwear was increasingly woven into the series. Whether he was shrugging on a shawl-neck cable-knit cardigan in season five, or wearing a selection of bold, block coloured knitted polos, Draper always had a way with the weave.

Our two favourite pieces from his woven wardrobe are the simple V-neck navy sweater, seen several times throughout the show’s second and third seasons (Aurélien do an amazing job at recreating the style), and his sleeveless cardigan, spotted in “Meditations in an Emergency” and uncannily similar to John Smedley’s ‘Huntswood’ design. Whichever you plump for, follow in Draper’s footsteps and layer it over a crisp white shirt, such as New & Lingwood’s.

The style lessons to learn from Mad Men’s Don Draper

Aurélien Merino V-Neck Sweater

£110

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The style lessons to learn from Mad Men’s Don Draper

New & Lingwood White Poplin Shirt

£125

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The style lessons to learn from Mad Men’s Don Draper

John Smedley ‘Huntswood’ Cardigan

£175

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