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Jell-O salads, smoking on planes: there are plenty of fads we left in the '60s. But like a good Eames chair, mid-century fashion never goes out of style. When Mad Men premiered in 2007, it became an instant classic, a Golden Age of TV juggernaut that won the hearts of fans and critics while setting countless trends in the process. Suddenly, lowball glasses and shift dresses were all the rage again, and it's a testament to the show's sense of cool that so many of its looks are still iconic fifteen years later. Whether you're new to Madison Avenue or on your third rewatch like I most definitely am not because that would be weird, we all could use a little Sterling-Cooper swagger in our lives. Just don't go pouring Old Fashioneds during your (Zoom) meetings. That went over a lot better back then.
DON DRAPER: The Man of the Hour
Superman has his cape, Lancelot has his armor, and Don Draper has his light gray suit. There's no look more synonymous with Mad Men's Man of Mystery than this impossibly suave vintage Calvin Klein number, but for those who missed out on the real-deal auction item, you're in luck. Proper Cloth's Allen Grey stretch wool suit ($695) is a dead ringer for Don's old faithful, with the same lightweight material and single-breasted cut. So grab one for yourself, throw it on, and tell Lucky Strike why their ideas aren't working. You'll look so good they just might listen.
If there's one thing Don Draper's gonna do, it's fill out a polo shirt. Season 2 gave us more glimpses of our hero off the clock, and this striking but neutral number is casual Draper at his best. J. Crew's Bowery navy tipped polo ($24.99) captures the same white trim around the collar that makes Don's look really sing -- because menswear, like advertising, is all in the details.
Of Don's many flaws, one that reared its head in every vacation episode is that the man cannot relax. Yet even when he packed his ennui as carry-on, he always left room for a knockout set of swim trunks. If you're searching for the same flair with color and pattern, look no further than OAS' purple tie swim shorts ($90.) After a harrowing period of boardshort supremacy, the swimwear world has caught back up with shorter hemlines, giving these trunks a cut that's both decidedly '60s and totally of the moment. Bonus points if you nab Don's very same Ray-Ban Olympian IIs ($172.)
BETTY DRAPER: Stepford Subverted
Restless, complicated, rarely satisfied, Betty Draper is a heartbreaker of a character, one who might've found more agency in a less repressive time. Her boldness always shines through, however, in her luxe sense of fashion. Take this stunner of a cashmere coat, one that communicates on sight that she owns 51% of this PTA Fund. We at TQE are big fans of Cuyana's leather goods, and now we're adding the brand’s wool cashmere short wrap coat ($345) to our cart as well. Cuyana is a brand that contains multitudes, not unlike Mrs. Draper herself.
If you live within three blocks of my apartment, you know I gasp every time I see Betty's Italian moment. The dress is right, the hair is right, but it's those earrings that are truly bravissima. These organic pearl hoops ($75) from Mejuri have the same amount of wow factor, offset by solid gold and a dynamic sense of movement. Why catch a jet plane when you can bring the magic to your doorstep?
Crying in a party dress -- the Robyn song writes itself. Betty's bold use of prints is nothing to shed tears over, though, and neither is the Faithful Eryn polka dot mini dress ($180) from Anthropologie. A modern silhouette with the same retro pattern, this look is the best of both worlds, and can be worn to outings a lot more festive than a Draper dinner party.
MEGAN CALVET: Tres, Tres Chic
I know what you're thinking: Megan gets higher billing than Peggy, than Joan?! Quel scandale! Yet if the thesis of Matthew Weiner's series is that people never change, this certified look queen reminds us that fashions always do. Her Quebecois heritage draws in influences from the French New Wave, and nowhere is that more evident than in the eye-popping fruit print she whips out on her and Don's trip to Hawaii. The whimsy of Lisa Says Gah's Pia mini dress ($159) makes it the perfect modern-day counterpart, an equally hip take on your trip to the farmers' market.
It's a natural fact that every time my partner invites coworkers over, I threaten to "'Zou Bisou Bisou' him." Yes, Megan made that song a verb in her stylish singalong from hell, trotting out this unforgettable black dress while serenading everyone Don's ever worked with. Whether or not your S.O.'s boss deserves you a cappella, Sezane's gorgeous Eve dress ($185) will make you the life of the party. Now excuse me while I brush up on the lyrics…
ROGER STERLING: The Silver Fox
While I can't prove that men around the world decided to let the gray in after getting one look at Roger Sterling, I stand firm in my belief. In a show chock-full of sharp dressers, Roger just might be the sharpest of them all, a man so debonair he brought the three-piece suit back from the dead. There's no three-piecer we love more than Reiss, and their Hope Modern Fit collection (jacket $495, waistcoat $240) would do the man with his name on the door proud. The word "waistcoat" never sounded so cool.
JOAN HARRIS: Queen of the Roost
The most ravishing redhead since Rita Hayworth, Joan Harris commands both fear and respect from all who cross her path -- as she damn well should. Joan's sharp-tongued takedowns and quotable mic drops are a high point of each episode, especially when she does it in her signature sheath dress. That confidence is hard to come by, but grabbing the Jillian dress ($265) from M.M.LaFleur is a start. A female-founded startup that specifically focuses on womens' workwear, M.M. has a similar philosophy to Joan's: that every office hallway can be your catwalk.
PEGGY OLSON: Miss Independent
Peggy Olson is, hands down, my favorite character on Mad Men -- the prickly, sarcastic, brilliant glass-ceiling crasher you root for from Episode One. As the brains of the operation, she's not generally the show's resident look queen, but there are few moments more badass than Peggy's defiant strut into McCann Erickson. Hard as it is to replicate the vintage pattern costume designer Janie Bryant hunted down, Rag & Bone's Peyton polo midi dress ($425) has the same spunky silhouette that demands a good power walk. Cigarette not included.
STAN RIZZO: Big-City Cowboy
I won't spoil who Stan ends up with in the finale, but like all good rom-com suitors, Stan starts off as the dude you love to hate. He may not even win you over by Season 7, but there's no denying he can rock some earth tones. A sharp counterpoint to the suit-and-tie crowd, Stan represents the changing tide of men's fashion, especially as the show inches towards the '70s. We have a feeling the corduroy work jacket ($165) from Alex Mill would get the Rizzo seal of approval -- it certainly has ours -- with a Stag Provisions leather bolo tie ($58) as the icing on the cake.
SALLY DRAPER: The Kids Are Alright
What better character to end our love letter with than Sally Draper? A wide-eyed onlooker to a world mired in chaos, over the seasons Sally grows up before our very eyes, oftentimes feeling like the show's beating heart. Like any teenager, she'll make sure to surprise you, and our jaws hit the floor when little Sally stunted in this Space Age-inspired mod mini dress. A fashionista rises!! For today's Sallys at heart, Salon de Yohn has the Silver Spangle mini dress ($181) that'll take you to the moon and back. Oh, you kids keep me young.
Matthew Weiner once said that Mad Men doesn't unfold like a novel; more like a collection of short stories. Consider these outfits entries into the canon -- brief, eye-catching vignettes whose stylish simplicity leaves you wanting more. While the days of Rolodexes and three-martini lunches may be behind us, there's always a good reason to scoop up some sixties-inspired fashion. If you get the urge for a rewatch while you're at it, then know you're in good company.
I'll save you a seat at the bar.
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