The Wrong Side of the Screen
What menswear missed while staring at Don Draper.
Finish a Mad Men rewatch and it’s easy to come away saying, “I’m going to dress like Don Draper.”
His looks, in and out of the office, have been the jumping-off point for plenty of well-deserved sartorial glazing. But much like in the show itself, the women get overlooked.
I’ve said this here before: it is easy to look great in a suit.
It is even easier when you look like Jon Hamm.
What the ladies of Mad Men offer is more useful than “wear a suit, look good.” They teach you how to dress for your life, your body, and your ambition.
So let’s turn our attention to the other half of the screen and bite into the good stuff: shape, trends, and how to never look out of place.
Trudy Campbell
Menswear is painfully fixated on versatility—the last one you’ll ever need. Wear it to the boardroom, the bar, the golf course, and then Chili’s with the wife and kids. This is not liberation. We keep burning our waistbands and replacing them with elastic, then calling it a carefree life. All that remains is polyester crap trying to fill every need and never making the grade.
The modern Trudy Campbell would have no interest in “the last pants you’ll ever need.” She would find the idea offensive.
She knows exactly what kind of life she wants, and dresses like she already has it. Understanding every room means knowing one pair of pants cannot answer every call. She doesn’t treat occasions like an inconvenience. She treats them as an excuse to elevate.
She doesn’t need ball gowns and pearls to be the cleverest person in the room. Never enough to make anyone else feel bad, but always a step above. Her garden-party look is the perfect example: a watercolor dress matched precisely to her bag, looking better than everyone there without upstaging the host.
She understands the difference between being comfortable and looking like you gave up. Even her nightgowns understood the assignment, if Pete never did.
Her well has endless water.
Joan Holloway
One thing we can all agree on about Joan is that she knows her measurements. Her clothes do more than merely flatter her, though. They give her authority. She leans into sharp, defined lines and colors that refuse to wash out her red hair. They put it to work.
I could cop out and give red all the credit. But look closer: the waist is exact, the skirts are narrow, the neckline is open but not soft, and the pen hanging at her chest lets you know she knows. Her tailoring commands the room. In a world that expects her to make herself small and unseen, Joan enters knowing she is inevitable.
At the Jaguar dealership, Don puts up a $6,000 check and the salesman lets them take the car out. Joan did the underwriting. A woman like that wasn’t getting into a car with a man whose checks bounced.
What we learn from Joan is not to wear tighter clothes. It’s that clothes should be precise. It doesn’t matter how expensive the clothes are if they’re in a civil war with your body.
I could turn this into a “dress for the body you have” after-school special. But this is prestige cable. Find your shapes and buy them. That does not mean buying the same pants in every color. Learn why they are so good—the rise, the width, the length, where they sit—and hunt for those qualities.
Pull your favorite clothes from the closet, measure them, and use them as anchors against size charts.
An appropriately unsexy ending to a section about Mad Men’s greatest sex symbol.
Peggy Olson
We are all Peggy Olson at some point: bright-eyed, bushy-tailed, and without the money or confidence to dress for our ambition.
Peggy changes the most. She arrives at Sterling Cooper dowdy, dressed for the job she has. As her ambition grows, the clothes catch up.
She is the anti-Joan, holding their breath and trying not to take up too much air. Rounded collars, frumpy skirts, muted colors—clothes praying to make it through the day without anyone noticing.
As Peggy becomes more confident, her clothes get bolder. There is no makeover montage where the cool girls take her ponytail down and suddenly she ends up in the ad. The change comes through little moments when we are asked to see her in a new light—the black dress with a pink bow that makes Ted rethink every choice he’s ever made. It all culminates in her Black Swan entrance: walking into McCann Erickson with sunglasses, a lit cigarette, and a vulgar Japanese painting tucked under her arm.
It is easier to dress to the expectations of others than to your own taste.
In my early 20s, I dressed in whatever fraternity-banquet clothes, Christmas Vineyard Vines, and TJ Maxx Ralph Lauren I already owned. The crown jewel was a gray Patagonia vest. This was a decade ago. It wasn’t as cursed yet.
Like Peggy, I was dressing to expectations. Once I started making money, that meant dressing “well” for my peers and the people who now worked for me. Usually by wearing something obviously expensive. The low point was a rose-gold Ferragamo logo belt. 2018 was a crazy time.
As I became more comfortable in my seat at the table, the fits followed. Sometimes misguided, but mine. Small revisions, but big changes—even if only to myself.
Betty Draper
Betty knows how to make eyes pop out of heads—look no further than the black outfit in Paris—but that is not where she shines. Her real talent is putting herself together for errands, afternoons around the house, and all the forgettable parts of the day most people treat as a sartorial write-off.
Betty Draper takes casual seriously.
The trophy still had to be polished. Even with no guests. Was that a healthy way to live? No. Did it produce an eye-popping road-trip fit? Of course.
The road-trip fit is simple: a sleeveless floral shirt, fitted shorts, and sunglasses. Nothing fancy. Nothing accidental.
Even off duty, in what you can only assume is a car with inferior air conditioning, Betty still looks ready to be seen.
Stop treating casual like an afterthought. Comfort is all well and good until you catch your reflection and realize comfort was the only decision you made. Don’t wear a neckerchief to meet the DoorDash driver, but give the ordinary some consideration. The clothes can unwind without collapsing.
Not every day needs an occasion, but every day deserves an outfit.
Megan Draper
RIP Megan Draper. You would have loved being an influencer. We would have loved watching you make Don do TikTok dances.
Megan had no interest in being anything but the moment. She was never wrong; she was just early. Her clothes moved, shimmered, and showed enough skin to occasionally caused Don a constitutional crisis.
Her outfits showed who she was in that instant. Hollywood starlet in the blue dress she wears to pick up Don, then starving-artist LARPing at her house in the Hills—the ultimate cool-girl move, deciding the city had nothing to offer her.
I’d love to talk hair and makeup, but I’m not qualified, and this is not the place to start pretending.
Not everything has to last forever, especially clothing. We all love to justify expensive purchases with a little cost-per-wear voodoo, but sometimes it’s more fun to be a prisoner of the moment. Everyone loves “quiet luxury,” a phrase that has regurgitated enough dupes to make me regurgitate. We worry so much about looking timeless that we forget to have any fun.
That does not mean chasing every trend until your card disintegrates. When something looks fun, take it for a spin—even if it is only for a night. You may think you are dressing timelessly now, but your taste will evolve, and eventually you will laugh at yourself anyway.
Dress for the moment. There is always tomorrow for your forever clothes.
The easiest lesson to take from Mad Men is to buy a charcoal suit and be handsome. To be fair, it works.
The ladies ask more of us. They ask us to know our measurements, read the room, dress for the person we are becoming, and give an ordinary Saturday a little respect. They also remind us to occasionally stop wondering whether something will still look good in ten years and wear the damn thing now.
So do your Don Draper cosplay. But once the suit hits the cleaners, keep watching.
The real lessons in the best-dressed show of all time were waiting on the other side of the screen.
-SP