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Mad Men’s Best Fashion Moments

By on May 25, 2015

January Jones as Betty Draper. Image © AMC

We recently bid farewell to one of the greatest shows on television, Mad Men. For seven seasons viewers followed the mad world of advertising and the lives of those working in Madison Avenue’s high rises during the 1960s. Along with those famous ad pitches were some seriously dated fashions, right?

Except in reality, the show was responsible for turning the modern fashion cycle back a few decades as 1960s trends became the rage all over again. In fact the costumes were so influential even Banana Republic released a Mad Men collection a few years ago. Mad Men began its run circa 1960 and ended in 1971, spanning an evolution in fashion from modest, shapely dresses to ‘how can anyone reach anything high in that?’ mini skirts to go-go boots, bikinis, and even pantsuits. And that’s just the women. When not wearing those dapper suits, the men of Mad Men always dressed down fairly nicely looking like very vintage J. Crew catalogues.

To celebrate the end of an era, we’ve chosen some of Mad Men’s best looks to see how they can be worn right now.


In the series finale, Don wears what has to be his most laid back outfit to date: a Levi’ denim jacket & (which can only be a Hanes) white tee combo. It’s such a far cry from how viewers have seen Don over the span of several seasons but it’s oddly refreshing. It’s definitely one of the most simple looks to pull off and, when done well, will look both chic and casual. It’s a true classic.

Levi’s denim jacket, H&M denim jacket, Rag & Bone tee, Topshop tee


Making a giant splash in the season 5 premiere, Megan Draper wore this flirty dress while giving a serenade no Mad Men fan will ever forget (Just try to get Zou Bisou Bisou out of your head now). While her dress in particular is fairly dated but may work for a evil witch Halloween costume, there’s plenty of ways to wear a black mini dress in every day life. Everyone knows the little black dress is perfect for every occasion from night’s out to even the workplace (when done appropriately), so add some sheer sleeves and you’ve got some serious Megan Draper vibes ready to go.

Missguided mini dress, Jill Stuart mini dress, Free People mini dress


Peggy Olson is a force to be reckoned with throughout the series, even when no one takes her seriously. She’s also had one of the biggest fashion evolutions of the series. She embraced the modest dresses of the 1950s, eventually grew to much more stylish dresses and even wore a pantsuit! She’s determined and hardworking and, this iconic scene from season 7, ready to take on the men on her power prints. The best part about this look is the prints can be worn in a subtle way (such as the black/white Ann Taylor) or bright and very 60’s inspired. Add some classic retro shades and voila!

Ann Taylor dress, Modcloth dress, Modcloth wayfarers, Ray-Ban clubmasters


Sally Draper had the greatest fashion evolution of any character simply due to her age. When Mad Men began her character was just turning 6 years old. The show ended when Sally was a teenager. Viewers watched her grow, learn, and while her fashion mainly consisted of trendy dresses, the dresses evolved with her. Here, having dinner with her dad before heading back to boarding school, she’s dressed in a mature looking jumper dress and turtleneck sweater. It’s not a full body shot but I assume she paired it with some nice looking socks & trendy mary janes.

J. Crew tee, Yumi pinafore, Anthropologie sleeveless turtleneck, Topshop pinafore


Betty Draper may not be the best mother on television or the best dressed mother on television, but this romper from season 1 is a stand out fashion moment from the series. The romper is an original piece by costume designer Janie Bryant made to be more carefree than most of Betty’s fashions and a nod to her past as a model. Rompers (or playsuits) are really comfortable warm weather options and while Betty’s is definitely more daring, there are great ways to channel this classic look for every day life.

Topshop print playsuit, Modcloth romper, Calvin Klein romper

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