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.

New & Lingwood Fine Stripe Grenadine Tie

New & Lingwood Fine Stripe Grenadine Tie

£95

Buy Now
Emma Willis Superior White Shirt

Emma Willis Superior White Shirt

£240

Buy Now
Drake’s Shantung Silk Grenadine Tie

Drake’s Shantung Silk Grenadine Tie

£145

Buy Now

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.

Ralph Lauren Plaid Silk-Blend Jacket

Ralph Lauren Plaid Silk-Blend Jacket

£520

Buy Now
Hackett Windowpane Check Blazer

Hackett Windowpane Check Blazer

£475

Buy Now
Paul Smith Check Wool-Silk Blazer

Paul Smith Check Wool-Silk Blazer

£750

Buy Now

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.

Monc ‘Lymington’ Sunglasses

Monc ‘Lymington’ Sunglasses

£230

Buy Now
TBD Eyewear ‘Vicuna’ Sunglasses

TBD Eyewear ‘Vicuna’ Sunglasses

£250

Buy Now
Cubitts ‘Calshot Fold’ Sunglasses

Cubitts ‘Calshot Fold’ Sunglasses

£125

Buy Now

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.

Sunspel Navy Cashmere Overcoat

Sunspel Navy Cashmere Overcoat

£650

Buy Now
Paul Smith Single-Breasted Coat

Paul Smith Single-Breasted Coat

£450

Buy Now
Loro Piana ‘Sartorial’ Coat

Loro Piana ‘Sartorial’ Coat

£4420

Buy Now

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.

Eton Shirts Black Bow Tie

Eton Shirts Black Bow Tie

£80

Buy Now
Turnbull & Asser Pleated White Cotton Dress Shirt

Turnbull & Asser Pleated White Cotton Dress Shirt

£300

Buy Now

Aspinal of London Black Mother-of-Pearl Dress Studs


Aspinal of London Black Mother-of-Pearl Dress Studs

£220

Buy Now

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.

Jaeger-LeCoultre Reverso Classic

Jaeger-LeCoultre Reverso Classic

£5650

Buy Now
Rolex Explorer

Rolex Explorer

£6000

Buy Now
Omega De Ville ‘Prestige’ Chronometer

Omega De Ville ‘Prestige’ Chronometer

£4200

Buy Now

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.

Aurélien Merino V-Neck Sweater

Aurélien Merino V-Neck Sweater

£110

Buy Now
New & Lingwood White Poplin Shirt

New & Lingwood White Poplin Shirt

£125

Buy Now
John Smedley ‘Huntswood’ Cardigan

John Smedley ‘Huntswood’ Cardigan

£175

Buy Now

Want more style guides? Here’s how to dress like Formula One legend Ayrton Senna…

Become a Gentleman’s Journal member. Find out more here.

Become a Gentleman’s Journal Member?

Become a Gentleman’s Journal Member?

Like the Gentleman’s Journal? Why not join the Clubhouse, a special kind of private club where members receive offers and experiences from hand-picked, premium brands. You will also receive invites to exclusive events, the quarterly print magazine delivered directly to your door and your own membership card.

Click here to find out more

Further reading