How to Shop for the 1960s

Posted by on May 23, 2011

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The success of Mad Men has created an obsession with the sixties. And what’s not to love? The clothes were glamorous and sophisticated and the workplace behavior was deliciously inappropriate. And while you may not be able to work for Don Draper or drink Scotch at your staff meetings, you can definitely look the part.

Shopping for vintage clothing can be even more fun than a visit to your favorite department store, especially since you can guarantee that no one else will be wearing your outfit (at least not in this decade!) If you don’t have many vintage stores or Goodwills where you live, there are tons of places to shop for fabulous clothes and accessories online.

But before you pull out your plastic, just a few words of caution:

— Be careful not to overdo it with a head-to-toe vintage look. You don’t want to look like an extra from The Mod Squad. Build your look around one amazing find, like a dress or a pair of shoes. A mix of vintage and contemporary pieces will give you an updated version of a '60s-inspired look that’s all your own.

— Most credible vintage sites will include information about the condition of a piece in the description, so you know exactly what you’re getting. But protect yourself and read up on the store’s return policy in case there are issues with fit or condition once you get it home. If you're shopping on Etsy (which has a great selection of vintage but usually offers no returns) be sure to check the sellers' feedback.

Now channel your inner Jackie Kennedy and let's go shopping!


Sixties fashion began where the fifties left off, with elegant and feminine silhouettes. Women rarely wore pants — even housewives were expected to do their dusting in a shirtwaist dress. Most dresses of the time had full skirts and cinched waists. In the mid '60s, the shift dress (with its loose fit and lack of defined waistline) took the spotlight.

Make It Your Own:


Skirts in the early '60s, like dresses, had modest hems that generally fell below the knee. The sleek pencil skirt and the fuller A-line were equally trendy during this time. Both skirts were commonly paired with a tailored blouse or a dainty cardigan, making the waist the focal point of the outfit. But by the mid '60s, women were pushing boundaries with their hemlines and the mini skirt emerged as a popular trend. It wasn’t uncommon to find skirts that were 4-5 inches above the knee.

Make It Your Own:

olive green wool houndstooth skirt
Olive Green Wool Houndstooth Skirt

A gorgeous olive wool pencil skirt never goes out of style. Stick with a top in the rich fall color palette. ($19.60, Tialey Vintage)
navy linen pencil skirt
Made-to-Order Navy Pencil Skirt

Make this lovely linen skirt part of your regular office wardrobe rotation by mixing and matching with a cardigan or a patterned blouse. ($95, DooliusSeizure)


Sixties shoes were either sexy stilettos or cute kitten heels. Go-go boots also appeared as a compliment to the mini skirt.

Make It Your Own:

brown suede lace up boots
Brown Suede Lace-Up Boots

Your leggings will love to hook up with a pair of amazing dark brown suede knee boots (that is, if you have the patience to lace them up!) ($70, Cherub Lover)


Women in the '60s typically chose coordinating handbags, hats and gloves to complete their looks. Since women were showing more leg with their shorter skirts, tights in a variety of colors and patterns replaced traditional ladies’ stockings.

Make It Your Own:

copper flower brooch
Great Vintage Jewelry
Copper Flower Brooch

Cheer up a fall blazer with this bright copper brooch. ($45, Great Vintage Jewelry)
black patent snake purse
Black Patent Snake Purse

Nothing says '60s like patent leather. This vinyl snakeskin handbag with gold metal frame has all of the qualities of a great everyday bag. ($40, GiRLStreetVintage)
1960 doctor bag
Vrseau Vintage
Doctor Bag

This tweed bag with leather trim and brass closure is ideal for the office. ($40, Verseau Vintage)
white angora fur hat
Some Like It Vintage
White Angora Fur Hat

Stay fashionably cozy in an angora fur bucket hat. Wear it with a tailored trench or mix it up with a puffy down coat. ($55, Some Like It Vintage)

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