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.

1960’s 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.

1960’s 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.

1960’s 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.

1960’s 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.

1960’s 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.

1960’s Mad Men Accessories

Purses

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.

Jewelry

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.

Hat

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:

 

Brighten Up Breakfast Dress
 

Brighten Up Breakfast Dress

$54.99

Buy at: ModCloth

Free People Womens Swinging 60's Dress
 

Free People Womens Swinging 60's Dress

$118.00

Buy at: Free People

Too Much Fun Dress in Cacti
 

Too Much Fun Dress in Cacti

$89.99

Buy at: ModCloth

Retro Printing Lace Splicing Sleeves Dress
 

Retro Printing Lace Splicing Sleeves Dress

$34.00

Buy at: ChicNova

1960s Style Mint Short Sleeve Stretch Mod Wiggle Dress
 

1960s Style Mint Short Sleeve Stretch Mod Wiggle Dress

$48.00

Buy at: UniqueVintage

eShakti Women's Tie neck poplin dress
 

eShakti Women's Tie neck poplin dress

$59.95

Buy at: eShakti

Retro Off-The-Shoulder Lace Dress
 

Retro Off-The-Shoulder Lace Dress

$25.53

Buy at: ChicNova

boohoo Robin Contrast Collar Dress - lilac
 

boohoo Robin Contrast Collar Dress - lilac

£16.00

Buy at: boohoo.com

An Afternoon With You Dress from ModCloth
 

An Afternoon With You Dress from ModCloth

$49.99

Buy at: ModCloth

eShakti Women's Shawl collar mod shift dress
 

eShakti Women's Shawl collar mod shift dress

$64.95

Buy at: eShakti

Regatta Go! Dress
 

Regatta Go! Dress

$54.99

Buy at: ModCloth

In Mod Daylight Dress
 

In Mod Daylight Dress

$54.99

Buy at: ModCloth

1960s Peace & Love Dress Adult Costume
 

1960s Peace & Love Dress Adult Costume

$34.99

Buy at: SpiritHalloween.com

Sass All, Folks! Dress
 

Sass All, Folks! Dress

$119.99

Buy at: ModCloth

Cobalt Contrast Collar Dress
 

Cobalt Contrast Collar Dress

$22.00

Buy at: Dorothy Perkins(US)

Land of Mod Dress
 

Land of Mod Dress

$129.99

Buy at: ModCloth

Dance Floor Date Dress in Dots
 

Dance Floor Date Dress in Dots

$59.99

Buy at: ModCloth

Sheen and Be Seen Dress
 

Sheen and Be Seen Dress

$94.99

Buy at: ModCloth

Too Much Fun Dress in Blue Dots - Long
 

Too Much Fun Dress in Blue Dots - Long

$99.99

Buy at: ModCloth

High Socie-tea Dress in Flower Box
 

High Socie-tea Dress in Flower Box

$129.99

Buy at: ModCloth

eShakti Women's Mod style crepe knit dress
 

eShakti Women's Mod style crepe knit dress

$51.95

Buy at: eShakti

eShakti Women's Mod style floral shift dress
 

eShakti Women's Mod style floral shift dress

$89.95

Buy at: eShakti

eShakti Women's Mod colorblock cotton satin dress
 

eShakti Women's Mod colorblock cotton satin dress

$79.95

Buy at: eShakti

Classic Act Dress
 

Classic Act Dress

$89.99

Buy at: ModCloth

A Very Speckled Occasion Dress
 

A Very Speckled Occasion Dress

$89.99

Buy at: ModCloth

Truly, Mod-ly, Deeply Dress
 

Truly, Mod-ly, Deeply Dress

$129.99

Buy at: ModCloth

eShakti Women's Colorblock cotton knit shift dress
 

eShakti Women's Colorblock cotton knit shift dress

$49.95

Buy at: eShakti

1960s Style Mod Super Spy Black Dress
 

1960s Style Mod Super Spy Black Dress

$68.00

Buy at: UniqueVintage

1960s Style Black Short Sleeve Stretch Mod Wiggle Dress
 

1960s Style Black Short Sleeve Stretch Mod Wiggle Dress

$48.00

Buy at: UniqueVintage

1960s Style Pink Short Sleeve Stretch Mod Wiggle Dress
 

1960s Style Pink Short Sleeve Stretch Mod Wiggle Dress

$48.00

Buy at: UniqueVintage

Amour Where That Came From Dress
 

Amour Where That Came From Dress

$59.99

Buy at: ModCloth

Burgundy Contrast Collar Dress
 

Burgundy Contrast Collar Dress

$22.00

Buy at: Dorothy Perkins(US)

1960s Style Pink & White Floral Halter Cut Out Scuba Flare Dress
 

1960s Style Pink & White Floral Halter Cut Out Scuba Flare Dress

$48.00

Buy at: UniqueVintage

1960s Style Black Long Sleeved Velvet Mod Bodycon Dress
 

1960s Style Black Long Sleeved Velvet Mod Bodycon Dress

$31.00

Buy at: UniqueVintage

Tall Ivory and Orange Colourblock Skater Dress
 

Tall Ivory and Orange Colourblock Skater Dress

$39.00

Buy at: Dorothy Perkins(US)

boohoo Lola Polka Dot Shift Dress - black
 

boohoo Lola Polka Dot Shift Dress - black

£16.00

Buy at: boohoo.com

eShakti Women's Tie neck cotton poplin dress
 

eShakti Women's Tie neck cotton poplin dress

$59.95

Buy at: eShakti

eShakti Women's Tie neck cotton poplin dress
 

eShakti Women's Tie neck cotton poplin dress

$59.95

Buy at: eShakti

boohoo Lori Retro Print 3/4 Sleeve Shift Dress - black
 

boohoo Lori Retro Print 3/4 Sleeve Shift Dress - black

£30.00

Buy at: boohoo.com

ASOS Swing Dress in Retro Floral Print - Print
 

ASOS Swing Dress in Retro Floral Print - Print

$46.00

Buy at: ASOS.com USA

eShakti Women's Retro style colorblock dress
 

eShakti Women's Retro style colorblock dress

$79.95

Buy at: eShakti

eShakti Women's Retro style colorblock dress
 

eShakti Women's Retro style colorblock dress

$79.95

Buy at: eShakti

Shimmer and Dancing Dress
 

Shimmer and Dancing Dress

$79.99

Buy at: ModCloth

Lace Collared Swing Dress
 

Lace Collared Swing Dress

$14.43

Buy at: ChicNova

Greenhouse Gallivant Dress
 

Greenhouse Gallivant Dress

$99.99

Buy at: ModCloth

All Amour Reason Dress
 

All Amour Reason Dress

$179.99

Buy at: ModCloth

eShakti Women's Asymmetrical collar ponte shift dress
 

eShakti Women's Asymmetrical collar ponte shift dress

$99.95

Buy at: eShakti

eShakti Women's Tulip embellished poplin shift dress
 

eShakti Women's Tulip embellished poplin shift dress

$69.95

Buy at: eShakti

eShakti Women's Nautical anchor embellished dress
 

eShakti Women's Nautical anchor embellished dress

$64.95

Buy at: eShakti

eShakti Women's Colorblock collar anchor print dress
 

eShakti Women's Colorblock collar anchor print dress

$58.95

Buy at: eShakti

Like Peas in a Mod Dress
 

Like Peas in a Mod Dress

$54.99

Buy at: ModCloth

Dahlia Drop Waist Dress With Removable Collar - Navy
 

Dahlia Drop Waist Dress With Removable Collar - Navy

$120.00

Buy at: ASOS.com USA

boohoo Cheryl Long Sleeve Collar Bodycon Dress - navy
 

boohoo Cheryl Long Sleeve Collar Bodycon Dress - navy

£26.00

Buy at: boohoo.com

Guest of Honor Dress in Vines from ModCloth
 

Guest of Honor Dress in Vines from ModCloth

$94.99

Buy at: ModCloth

Plus Size 1960s Style Black Long Sleeve Fitted Mod Wiggle Dress
 

Plus Size 1960s Style Black Long Sleeve Fitted Mod Wiggle Dress

$52.00

Buy at: UniqueVintage

Navy Contrast Collar Dress
 

Navy Contrast Collar Dress

$22.00

Buy at: Dorothy Perkins(US)

Just in Timeless Dress in Blossoms
 

Just in Timeless Dress in Blossoms

$124.99

Buy at: ModCloth

Mela White Check Print Collar Dress
 

Mela White Check Print Collar Dress

$22.00

Buy at: Dorothy Perkins(US)

Yellow waffle collar shift dress
 

Yellow waffle collar shift dress

$28.00

Buy at: Dorothy Perkins(US)

Dream Dot Dress
 

Dream Dot Dress

$49.99

Buy at: ModCloth

Vibrant Valedictorian Dress
 

Vibrant Valedictorian Dress

$79.99

Buy at: ModCloth

Daytrip Darling Dress in Confetti
 

Daytrip Darling Dress in Confetti

$104.99

Buy at: ModCloth

Sophisticated Situation Dress in Black
 

Sophisticated Situation Dress in Black

$54.99

Buy at: ModCloth

What Does the Fox Wear Dress
 

What Does the Fox Wear Dress

$99.99

Buy at: ModCloth

Work to Play Dress in Navy
 

Work to Play Dress in Navy

$54.99

Buy at: ModCloth

Work to Play Dress in Eggplant
 

Work to Play Dress in Eggplant

$54.99

Buy at: ModCloth

Right on Timeless Dress in Black
 

Right on Timeless Dress in Black

$54.99

Buy at: ModCloth

Day Trip Dreaming Dress
 

Day Trip Dreaming Dress

$99.99

Buy at: ModCloth

boohoo Mollie Mono Check Collar Shift Dress - black
 

boohoo Mollie Mono Check Collar Shift Dress - black

£20.00

Buy at: boohoo.com

Tender Loving Character Dress
 

Tender Loving Character Dress

$99.99

Buy at: ModCloth

1960s Style White Short Sleeve Stretch Mod Wiggle Dress
 

1960s Style White Short Sleeve Stretch Mod Wiggle Dress

$48.00

Buy at: UniqueVintage

Flourish of July Dress
 

Flourish of July Dress

$129.99

Buy at: ModCloth

Too Much Fun Dress in White Dots - Long
 

Too Much Fun Dress in White Dots - Long

$99.99

Buy at: ModCloth

Too Much Fun Dress in Cocktails
 

Too Much Fun Dress in Cocktails

$89.99

Buy at: ModCloth

1960s Style Rainbow Fringe Mod Dress
 

1960s Style Rainbow Fringe Mod Dress

$75.00

Buy at: UniqueVintage

Too Much Fun Dress in Airplanes
 

Too Much Fun Dress in Airplanes

$89.99

Buy at: ModCloth

1960s Style Black Long Sleeve Bettina Fitted Knit Pencil Dress
 

1960s Style Black Long Sleeve Bettina Fitted Knit Pencil Dress

$108.00

Buy at: UniqueVintage

Greenhouse Gallivant Dress in Forest
 

Greenhouse Gallivant Dress in Forest

$89.99

Buy at: ModCloth

Evening Glow Dress in Shiraz
 

Evening Glow Dress in Shiraz

$124.99

Buy at: ModCloth

Blue & White Stripe Sleeveless Cut Out Nautical Fit & Flare Dress
 

Blue & White Stripe Sleeveless Cut Out Nautical Fit & Flare Dress

$55.00

Buy at: UniqueVintage

Ganni 60s A Line Dress with Frill - Emerald green
 

Ganni 60s A Line Dress with Frill - Emerald green

$211.00

Buy at: ASOS.com USA

Warehouse 60s Shift Dress - White
 

Warehouse 60s Shift Dress - White

$92.00

Buy at: ASOS.com USA

1960s Style Mod Black & White Cap Sleeve Stretch Annie Dress
 

1960s Style Mod Black & White Cap Sleeve Stretch Annie Dress

$82.00

Buy at: UniqueVintage

1960s Style Yellow & White Mod Color Block Stretch Flare Dress
 

1960s Style Yellow & White Mod Color Block Stretch Flare Dress

$48.00

Buy at: UniqueVintage

1960s Style Grey, Teal & Pink Dandelion Floral Gwendolyn Flare Dress
 

1960s Style Grey, Teal & Pink Dandelion Floral Gwendolyn Flare Dress

$98.00

Buy at: UniqueVintage

1960s Style Pink Lemonade Printed Mod Shift Dress
 

1960s Style Pink Lemonade Printed Mod Shift Dress

$98.00

Buy at: UniqueVintage

Observation Versus Influence Dress
 

Observation Versus Influence Dress

$69.99

Buy at: ModCloth

Suppose You Pose Dress in Teal
 

Suppose You Pose Dress in Teal

$64.99

Buy at: ModCloth

Prairie Portrait Dress
 

Prairie Portrait Dress

$84.99

Buy at: ModCloth

1960s Style White, Red & Black Ladybug Print Sleeveless Flare Dress
 

1960s Style White, Red & Black Ladybug Print Sleeveless Flare Dress

$88.00

Buy at: UniqueVintage

1960s Style Red & White Striped Nautical Shop Till You Drop Wiggle Dress
 

1960s Style Red & White Striped Nautical Shop Till You Drop Wiggle Dress

$88.00

Buy at: UniqueVintage

1960s Style Navy Blue & White Striped Nautical Shop Till You Drop Wiggle Dress
 

1960s Style Navy Blue & White Striped Nautical Shop Till You Drop Wiggle Dress

$88.00

Buy at: UniqueVintage

1960s Style Mod Super Spy Navy Dress
 

1960s Style Mod Super Spy Navy Dress

$68.00

Buy at: UniqueVintage

1960s Style Yellow & White Crochet Embroidered Short Sleeve Sunshine Day Swing Dress
 

1960s Style Yellow & White Crochet Embroidered Short Sleeve Sunshine Day Swing Dress

$58.00

Buy at: UniqueVintage

Prim and Playful Dress
 

Prim and Playful Dress

$54.99

Buy at: ModCloth

Bada Bing, Bada Bloom Dress
 

Bada Bing, Bada Bloom Dress

$94.99

Buy at: ModCloth

1960s Mod Style Black & White Trim Short Sleeve Fitted Wiggle Dress
 

1960s Mod Style Black & White Trim Short Sleeve Fitted Wiggle Dress

$58.00

Buy at: UniqueVintage

1960s Style Navy Short Sleeve Stretch Mod Wiggle Dress
 

1960s Style Navy Short Sleeve Stretch Mod Wiggle Dress

$48.00

Buy at: UniqueVintage

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About Debbie Sessions

Debbie Sessions is passionate about wearing history through fashion. She and her husband, 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 more 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}

    Reply
    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!)

      Reply

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