1960’s Mad Men Dresses and Clothing Styles

Mad Men Dress

Ever since AMC’s TV series Mad Men went on the air there has been a lot of demand for vintage and vintage inspired early to mid 1960’s Mad Men dresses. Classy ladies love the sexy pencil dresses worn by Joan while our hearts resonate with Peggy’s innocent personality and cute retro style. Even Betty’s housewife glam is something to “ooo” and “ahh” over.  Thankfully modern designers have rescued us from moth-eaten vintage frocks and brought back the fashions of the 60’s with modern mad men dresses. Let’s take a look at a few of the classic Mad Men clothing styles available today and where to buy them:

P.S. This is for the ladies. Men go here learn how to dress like Don Draper and the rest of the Ad Men crowd.

1960s Mad Men Sheath Dresses- The Secretary Style

pin up dresses

1960’s Cocktail Dress

While most women didn’t wear their dresses as tight as Joan did, women were into form flattering pencil shapes. The pencil dress and pencil skirt came in various lengths. Your body shape will decide which length is appropriate for you- not your office morals : ) These were not meant to be worn tightly, rather the shape of the dress loosely outlined your natural body shape. Skirts had kick pleats on the back so that you could walk comfortably, not hobble down city streets.

Waist lines were still high up compared to later decades. Having a tight, tucked, thin waist had been in fashion since the 1940’s and it wasn’t going to go away anytime soon. Proper waist cinching undergarments were a must for all clothing of this era.

mad men pink dresses

1960’s Vintage Dress

To add a vintage 60’s inspired sheath dress to your wardrobe simply look for a high round neck bodice and shapely  fittesd skirt. If you see one with a rounded collar or cute side tie- grab it fast. Colors range to suit you best. Plain colors more then patterns were seen on this style of dress. Formal occasions added more shine with jewel tone materials.

These sheath dresses are also called short cocktail dresses. Although the little black dress was develop in the 1920’s it really took off in the 1950’s and 1960’s. Think Breakfast at Tiffany’s.

By season 4 of Mad Men we start moving into the mid 60’s with plenty of vibrant colors. This is the time where we start to see a lot of bright orange, green, yellow and  loud plaids. Yikes! The sheath dress was still popular but a little less form fitting and more straight on the body. Mad men dresses still flattered the body and maintain the personality of the characters. So should yours.

1960s Mad Men Dresses: Full Circle Dresses

Full Circle Dress

The full circle dress or swing dance dress is what Betty and every 1950’s housewife wore. They remained popular into the early 1960’s although perhaps a little less full then in the early 50’s. The most common style of dress was the shirtwaist. It buttoned down the front like a blouse, fitting snugly over layers of underwear and slips, and then layed out over yards of gathered tulle. House dresses came in many patterns of checks, plaids, and flowers. The later into the 1960’s the brighter the colors became and the less tulle petticoats were worn.

At the office these dresses were worn with only a slip- no huge petticoats. Peggy is the champion of the office style circle dress. A bit dated from the 1950’s, she didn’t quite fit into the modern look. Towards the final third season her style took on more buttons and bold patterns to reflect her evolving fashionable personality.

1960s Mad Men Clothing: Women’s Pants

Cigarette Pants

Other then a scene with Betty- women’s pants were not worn on Mad Men. It’s a shame because cigarette pants are simply adorable and flattering on more body types than the popular 1950’s Capri pants. Cigarette pants were usually black, flat front, and narrow down to the ankle. They remind me of long Capri’s and are often confused with each other. They are slim but not quite as body hugging as skinny pants are today. They are sometime called ankle pants or crop pants.

1960s Mad Men Clothing: Shirts, Tops, Blouses and Sweaters

Paisley Lace Top w/Peter Pan Collar
When a women wore pants or a pencil skirt is was always worn with an ultra cute top. These could be button down blouses for a more casual look, or pull over sweater tops that buttoned at the back or shoulder. The plain fronted top with  various styles of collars and ties were quite becoming on women in the 1960’s. A slightly more conservative woman may wear a matching top and cardigan sweater called a twin set. These pretty soft knit sweaters usually button on the top only exposing the short sleeve shirt underneath. These are highly loved and collected today. If you also watch Glee you will see Miss Phillsburry wearing twin sets with pencil skirts.

1960s Mad Men Clothing: Women’s Shoes

1960’s Shoes

Kitten heels or classic pumps were all that women wore in the office and believe it or not at home too! Kitten heels are small, narrow heels on short, almost flat like pumps. Decoration was minimal in favor of shoes that matched your dress perfectly. Toes were pointed instead of round and never had ankle or foot straps. A slingback was still OK for summer. Sandals were present but not popular. Shop for 1950’s / 1960’s womens shoes.

1960s Mad Men Accessories


Lucite Clutch

Purses always matched a Mad Men outfit.  It was a signature of a well polished lady. The signature style for day wear was a flat, square or slightly rectangle shape, leather purse with a single arm strap in either leather or gold chain. For evenings or special occasions plastic Lucite clutch purses were a short lived but very big fad in the early 60’s. These cute rounded bags opened with a clasp or had a short gold chain. Fabric or leather clutches were also common and also always matched the dress.


Gold Brooch

If you have a mother or grandmother who was a young women in the 1950s and 1960’s then you probably have noticed that they still wear a strand of pearls with their dresses. Pearl necklaces were the item to have and wear. The fad was started by Jackie Kennedy and remained very popular throughout the 50’s and 60’s. I’m sure other gold jewelery was worn but the pearls were a stamp of fashion and sophistication.

The other popular jewelry element was the brooch or pin. Usually gold or accented in pearls every dress, sweater or jacket wore one on the upper right side. Flowers and leaves, sometime animals, were shaped into fancy gold pins. Colorful gems acted as the flower center with sprays of gold petals surrounding it. Evening wear was extra sparkly with rhinestones or fancy small diamonds throughout the design. Buy some reproduction 1950’s jewelry here.


This was the last decade where a woman wasn’t a woman if she didn’t wear a hat. In the show we didn’t see women wearing hats much since they took them off in the office. To and from work was a different story. Women’s hats came in a variety of shapes and styles. Felt was the main material, shaped into cloche like hats with wide brims, or sculpted into angular shapes and balanced at an angle. One unique shaped hat style had a crescent shape to it that pinched the head on either side of the head leaving the back of the head uncovered. These were ideal for hairstyles, like Joan’s french twists because it didn’t mess up the hair when taken off.

Start Shopping!

Here are some nice 1960’s Mad Men dresses and accessories to help you start your Mad Men clothing wardrobe:

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About VintageDancer

Debbie & Oscar have turned their hobby into a career by teaching others how to re-create vintage style with affordable new vintage inspired clothing and accessories. We connect shoppers to the best vintage inspired clothing, shoes and accessories and teach fashion history as it was worn by everyday people. Need help? Contact us anytime.

2 thoughts on “1960’s Mad Men Dresses and Clothing Styles

  1. Samantha Gray

    I grew up in he 1950’s and was in my late teens and twenties in the 1960’s. Incredible time to be alive with sooo much history in the making! Pearls were The Thing, as you correctly point out. But somethign you missed mentioning were circle pins. In the early to mid 60’s they were HUGE. The pins were circles, some had chasing engraved, some had tiny enamel flowers, etc – usually only one sitting on the circle itself. I still have mine: slender gold circle with a cloisonne. peridot green butterfly. Classic items never go out of fashion! ;0}

    1. Debbie Sessions Post author

      Excellent addition. Thank you! Jewelry is not my area of expertise so I am always glad to hear about what I missed, especially from a direct source (the best kind of history!)


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