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Sally Draper

The series' smallest style star, Betty's daughter (played by the wonderful Kiernan Shipka) favors twee touches like satin headbands and patent flats that are both age-appropriate and adorable. Click through to shop her look.

A bow-tied headband adds the perfect amount of sweetness.

Sally loves a colorful capri pant.

Perfect for wearing under loafers, flats or pumps.

Rachel Menken

One of Don's first-season love interests, Rachel owns Menken's department store and asks Sterling Cooper to help revamp the image of her family business. Click through to shop her look.

Who could forget the dramatic feathered hat Rachel wears in her introductory scene? This headband offers the same look—and is just a touch more toned-down.

Perfect for a consultation (er, romantic rendezvous) with Don.

Ever classy, Rachel favors statement—but never over-the-top—jewelry, like beaded necklaces and sparkling brooches.

Trudy Campbell

Peter's devoted wife, Trudy, knows just how the corporate machine works—and is willing to do just about anything to help her husband climb the professional ladder. She's also really, really good at dancing the Charleston. Click through to shop her look.

The picture of an Upper East Side blueblood, Trudy's never without her classic pearls, wearing them on her ears, neck and wrist in almost every scene she's in.

A picnic-perfect pick.

Polished yet punchy, just like Trudy herself.

Bobbie Barrett

The "wifager" (that's wife and manager) of brash comedian Jimmy Barrett, Bobbie begins an affair with Don just after her husband teams up with him on a business deal. She's smoking hot...and knows it. Click through to shop her look.

For Bobbie, a slinky red dress is a cocktail party non-negotiable.

This character's accessorizing M.O.? Don't wear it unless it makes a major impact.

Metallic brocade is just about as demure as Bobbie ever gets.

Jane Sterling (née Siegel)

Shortly after being hired as Don's secretary at Sterling Cooper, Jane becomes the object of Roger Sterling's affections. The two marry, despite Jane being about the same age as Roger's daughter. But hey, the girl's got style. Click through to shop her look.

Remarkably similar to the scarf-neck blue dress Jane wears when she first catches Roger's eye.

A bold, classic red lip is this ex-secretary's beauty signature.

Nobody can pull off a statement hat like this lady.

Midge Daniels

Don's beatnik girlfriend from Season One, artist Midge, is totally fine with keeping her relationship with Don casual. Her boho approach to dressing is similarly easy-breezy. Click through to shop her look.

A striped baja top? Totally Midge.

Artsy, and for such a good cause.

The full silhouette makes this skirt '60s-appropriate, while the tribal pattern is unquestionably bohemian.

Joyce Ramsay

Photo editor Joyce befriends Peggy in Season Four. The first lesbian character in Mad Men history, she rolls with an artsy crowd and might have more-than-platonic feelings for her new Sterling Cooper pal. Click through to shop her look.

A little bit beatnik, a little bit business.

Joyce loves a well-cut blazer.

Considering she and Peggy first bonded over the subject of nude photography, we suspect Joyce might love Helmut Newton's controversial work.

Suzanne Farrell

Sally's schoolteacher, Miss Farrell, is yet another one of Don's conquests. Unfortunately, she later falls victim to his identity crisis. Click through to shop her look.

Just like the off-the-shoulder green dress Suzanne wears in the solar eclipse episode—when she and Don first get together.

As a teacher, Miss Farrell's constantly running around—which means ballet flats, not heels, are the best footwear option.

Era-appropriate outerwear for the next time Don leaves her out in the cold. If there is a next time, that is.