How to Dress Like "Mad Men"

We can’t help but love the trophy-wife look of Betty (played by January Jones). Sure, we like the idea of a trophy husband, too, but we’d love to slip on this tailored, floral sheath and pretend, if even for a half-hour, that our biggest role was simply to look like the prim lady of the house.

(Keep going to get Betty’s look.)

Warm coral hues look great against the skin, especially with the flattering silhouette of this A-line skirt. A ruched bodice is always forgiving; and here the crinoline detaches, so you control the poof.

Vintage floral cotton swing dress, $146; unique-vintage.com

In a decade where showing too much skin wasn’t just tacky but verboten, Joan (played by Christina Hendricks) is a prime example of how sex pots got by. Crepe dresses like this are simple and rely on showcasing the most vintage accessory of all: the hourglass figure.

A keyhole neckline avoids indecent exposure, but gives a peek-a-boo glimpse of skin that’s sweetly sexy. Demure polka dots at the sleeves and neck help tone down the bombshell bits. Our favorite touch is the waist detailing, providing a faux belt that better defines your shape.

Red and black keyhole dress, $178; unique-vintage.com

“Good girl” is written all over Peggy, the character played by Elisabeth Moss. Some of Peggy’s stylings are too retro to work today (floppy bow tie, Peter Pan collar), but others will meld perfectly with your wardrobe: strong prints, like these graphic red roses, and three-quarter sleeves—which also serve as a handy cover-up for a common problem area.

When plaid is done like this, in a simple shape and with conservative coverage, it’s perfect (without making you look like a lumberjack wannabe). Deep colors, grounded in black, give it grown-up appeal.

Vintage plaid swing dress, $128; unique-vintage.com

Even the girliest faces get an added air of maturity when wearing a dinner dress. Rich brocades lend pizzazz to simple styles, and the thicker fabric keeps the shape of the dress (and acts like a barely there corset). Black and gold is a color combo as relevant in Don Draper’s day as it is now. And the brooch? Two words: Michelle Obama.

Satin is pretty, feminine and flirty, and, like brocade, it looks luxurious. The large, swooping roses on this dress are simply too chic for a garden party and will make any woman find a party to attend, pronto.

Gold floral lace illusion dress, $68; unique-vintage.com

There’s an undeniable Grace Kelly quality to the way Betty wears her clothes. When worn with sophisticated hair and makeup, the bright colors and jeweled embellishments are nothing to fear. So wear color—if Betty can, you can, too.

Betty might have been dressing to please her husband, but we suggest pleasing yourself instead. And don a devil-may-care attitude: If a color or style grabs your eye, try it!

Vintage aqua tulle party dress, $118; unique-vintage.com