Style lessons from: Don Draper, Mad Men
There's a lot to learn from the sleekest, chicest ad man in town.

THERE’S A LOT we can learn from Donald Francis Draper of Mad Men fameâthe good, the bad, and often the ugly. A caricature of inspiration and creativity but not necessarily the man we should strive to be as while he commanded attention, the advertising exec rarely let people in. But if there’s one aspect of Draper’s life we can adopt, no questions asked, it’s his inherent sense of style.
Welcome to Esquire’s style lesson with Don Draper.
The world was first presented to the well-dressed, well-coiffed ad man in 2007 when the Emmy-winning drama, Mad Men, aired its first of 92 episodes. The very first scene sets the tone for the series of events to unfold: it’s the early ’60s, advertising agencies were on the rise, smoking was cool, and here is this debonair yet mysterious man, confident yet not aloof, sitting alone in a booth in a grey wool suit with thick lapels and wide shoulders, a perfectly-ironed white pointed collar shirt and a patterned silk tie to match. Draper orders an old fashionedâhis signature drink for the entirety of the seriesâand chats with his waiter for inspiration on a smoking ad he is working on, as detailed by the notes he takes on the back of a napkin.
It’s hard not to fawn over the clean-shaven, slick hair pomaded Draper who, from the outside, represents the quintessential American man of the time. Mad Men, along with Draper, in a way helped ignite the whole #menswear era of the 2010s, and was a key driver in bringing back tailored suits, pocket squares, monk-strap dress shoes, classic barber cuts and an appetite for vices in whisky and smoking.
Sure, menswear, in particular suiting, has changed drastically since Mad Men aired its final season in 2015. Suits (and ties) are scarcely worn in the workplace, and the silhouettes that make up tailored-wear are now free-flowing and relaxed, as opposed to the rigid nature of suiting from the ’60s and ’70s. But even if it has been eight years since the last episode of Mad Men played out its final episode, there’s still an appetite, a curiosity, for all things Don Draper.
Here are nine style lessons to learn from Don Draper, applicable in 2023.

1
Don’t underestimate the importanceâor powerâof a well-tailored suit
Yes, the way menâand womenâwear suits in 2023 is very different to that of Man Men era. But there is a universal lesson to take from Draper’s wardrobe: every man should own a well-tailored suit. Sure, you might find yourself only needing to wear a suit a number of times per year, but when you do, why not look and feel your best, Ă la Don Draper.
âDonâs colour palette is all about masculinity, seduction and mystery,â Mad Menâs costume designer, Janie Bryant, told Forbes. âI always felt like all of those grey suits were like his armour. That suit, it protects him.â

2
Know how to wear a sports jacket
If Draperâs suits were impactfulâit was what he wore 90 per cent of the timeâseeing him “dressed down” in a sports jacket and open shirt was a welcomed surprise. An easy way to elevate your look for smart-casual affairs, and one that will never go out of styleâmaybe just be wary of the garish sixties-style checks and prints.

3
Dress watches are timeless
We learn pretty early on that Don Draper is a watch guy. Specifically, he has a penchant for fine dress watches. While this was the signature watch of any man in the ’60s and ’70s, Draper shows just how enduring this watch style can be. In the second season, he celebrates a promotion with a Jaeger-LeCoultre Reverso Classicâone of the most popular dress watches to this dayâand the last few seasons of the show, he is mostly seen wearing the Omega Seamaster DeVille.

4
Respect your creativity
Very early on, we learn that Draper is a man plagued with internal struggles, such as regret, guilt, and identity. On the outsideâand one trait he wholly ownsâis his ability to be creative and let his creativity inform important business, and life, decisions. This, in turns, bolsters his confidence which makes him a formidable leader in his workplace. Draper is professionally questioned and doubted over many seasons, but he always allows the time to nurture his creative process to prove naysayers wrong.

5
Own a bomber jacket
Bomber jackets have been worn by men as far back as World War One. Over a hundred years later, bomber jackets continue to remain a universal wardrobe staple thanks to their inherent style, versatility, and function. Oh, and is there anything cooler than a bomber jacket paired with aviators at the weekend?

6
Grooming is important
While we’re unsure whether Draper was a man who would cleanse and moisturise on the daily, there’s one grooming aspect he had down pat: his hair. There’s a few lessons to be taken from this instance: find a good barber and build a rapport (it’s incredibly hard to find a qualified barber that will take the time to learn how to best work with your hair). Learn what hair style works for you and stick with it. And finally, invest in good hair product. While the slick side-part might not be your cup of tea, don’t be a stranger to experimenting with different styles of hair product to perfect your look.

7
Invest in a signature, statement pair of sunglasses
This is a pretty obvious style lesson, and by looking at the supported image, you can tell why. A good pair of shades made for your face shape and frame, is a priceless investment.

8
Read before bed
Mobile phones didn’t exist in the ’60s so Draper wasn’t one to doom scroll before bed. Instead, he was partial to a good novel before sleep, which undoubtedly helped inform some of his creative decisions that were considered progressive for the time. Don’t underestimate the power of a good bookâor winding down before some much-needed shut eye.

9
Embrace your inner zen
By the end of the seventh and final season of Mad Men, Don Draper comes to find a level of peace and clarity within his life. After many long years of soul searching, he finds solace in the form of yoga and mediation. Don’t be afraid to unlockâand embraceâsome zen in your life. It could very well do you wonders.