‘Mad Men’ Fashion: Joan Holloway’s Most Iconic Style Moments

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It would require two hands to count how many Joan Holloways I’ve encountered on Halloween over the years. Her look is iconic: red hair in an up-do; a curve-hugging, short-sleeved, gem-toned ponte dress with a pencil skirt and a cinched waist; a gold brooch; her signature pencil necklace; and a fierce strut through the halls of Sterling Cooper.

But Joan Harris, she’s a more sophisticated woman. She gets married, has a baby, gets divorced, makes partner. She starts wearing bright prints and quirky, feminine business suits, still with her brooches and other bold accessories. By season 6 and 7, Joan is — gasp — wearing her hair down and experimenting with bangs. It’s almost as if she’s entered the ’60s just as the ’60s are ending. Joan’s style evolution is the most subtle of all the leading ladies on Mad Men, which kicks off the second half of its seventh and final season this Sunday.

“She has some progressions, but her figure really is suited for that Fifties design and silhouette,” Mad Men costume designer Janie Bryant told Vanity Fair . “Christina [Hendricks, who plays Joan] and I always joke that Joan buys her clothing two sizes too small. It’s always about accentuating her hourglass. I’ve always seen her as this character who asserts herself in a very feminine way in the office. And she understands how to use those assets. She really holds onto that late-fifties moment. I always thought Joan’s style icons would be Marilyn Monroe and Sophia Loren. Those women who always exude sexiness.”

Let’s celebrate the kind of woman Joan personifies by revisiting ten of her most iconic looks throughout Mad Men so far.

Two Green Dresses

The pilot (up top) and throughout season 6 (bottom)

In the show’s first episode, “Smoke Gets In Your Eyes,” Joan Holloway wears a snug emerald green dress with a pencil skirt, a boatneck, a belt at the waist, and a gold brooch. The styling isn’t quite there on her hair and makeup, but the first time we see Joan, she’s wearing the quintessential outfit now widely associated with the character. By season 6, Joan’s emerald green dress is even more flattering, on top of being sassy and contemporary. Over the years, Joan’s style has evolved slightly, but she’s still following her own advice from the pilot: “men love scarves.”

Showing Off The Ring

Season 2, Episode 5 — “The New Girl”

When Joan gets engaged to Greg, she puts on a nice face and an even nicer dress the following day at work. Some of Joan’s best looks find her wearing royal blue, which wouldn’t be the first color some associated with Holloway (that’d more likely be red or green). But with her signature gold pencil necklace and a waist cinched with a bow, this look is classic Joan.

The Rape Scene

Season 2, Episode 12 — “The Mountain King”

For one of the most emotional Joan episodes ever, Mad Men costume designer Janie Bryant gave her a rare color-block moment. The shades of purple vary so slightly yet don’t clash, it’s clear a lot of thought went into creating a look that would stick in viewers’ mind, much like the traumatizing rape scene between Joan and then-fiancé (!!!) Greg.

Humiliation via Asshat and Accordion

Season 3, Episode 3 — “My Old Kentucky Home”

As Joan’s marriage to Greg is on the rocks, she’s forced to play the dutiful hostess for her husband’s guests. He has the nerve to make her play the accordion at their dinner party, which embarrasses her greatly, but least she looks feminine, fashionable, and all-around stunning doing so. “It’s a degrading moment,” Mad Men costume designer Janie Bryant told The New York Daily News of the scene. “There are two things going on in that scene. The roses represent Joan’s optimism for love and romance, but the black is more serious and sad.”

Midnight Cool

Season 3, Episode 13 — “Shut the Door. Have a Seat.”

In one of the greatest Mad Men episodes ever, Sterling Cooper Draper Pryce is formed via clandestine meeting late at night. Joan is asked to join the new agency, and shows up to the office for said meeting looking chic as ever. This is the only time Joan wears pants to the office, but with how Audrey Hepburn classic she looks, it should really be considered more often, despite how un-Joan-like it may be.

Wrapped Up In Red

Season 4, Episode 2 — “Christmas Comes But Once a Year”

Joan wears so many body-hugging, fire-engine-red dresses throughout the series, they all start to blend together into one flawless vision. But only one of them inspired a line of dialogue from showrunner Matthew Weiner. After he saw the dress, Weiner had Roger Sterling tell Joan to wear this specific dress at the company Christmas party, referring to it as, “the red dress, the one with the bow on the back, that makes you look like a present.”

“I showed him a picture from our fitting with Christina and he loved it so much that he said, ‘I’m going to write a line in there about the bow,’” Mad Men costume designer Janie Bryant told The New York Daily News . “It’s good when we inspire each other.”

The Comeback

Season 5, Episode 1 — “A Little Kiss”

Joan worries for her job security while finishing up maternity leave, so she pops by SCDP for a visit with baby Kevin — and an unreal post-baby body, as Meredith points out — in tow. After having been cooped up for months and at odds with Greg, it’s clear Joan was looking for an opportunity to get dolled up and show off. She does just that with this satin printed dress; my favorite detail are the bejeweled sleeve edges.

Strictly Business

Season 5, Episode 11 — “The Other Woman”

Joan is offered $50,000 to sleep with Herb, the owner of a Jaguar dealership that can make or break the agency’s chances at the elite car brand’s business. She wants to be a partner in the agency, however. When you see how sexy Hendricks looks when the bribe goes down — complete with an emerald necklace from Herb — it’s hard not to think that Sterling Cooper got a deal on the whole thing. It’s not often that Joan wears all black (or goes that simple in her accessorizing), but when she does, she stuns.

Well Hello, Elizabeth Taylor

Season 6 promo photos

Why Joan never wore this ball gown in an episode from season 6 — instead of just in the much-discussed promo photos released before the premiere — is likely because she had nowhere to wear it: season 6 saw Joan Leaning In at work, balancing her motherhood responsibilities (Greg is long gone by then), and getting cozy with Bob Benson. Still, this gown sticks with me as a traditional glamour moment for the show’s most traditional glamour girl.

Joan’s Take On The Swinging Sixties

Season 6, episode 10 — “A Tale of Two Cities”

As Mad Men progressed through the ’60s, Joan’s silhouettes stayed mostly in the ’50s. Bold patterns, however, were used to show her keeping up with the times in her own signature way. When Joan goes to meet an Avon marketing rep for what she thinks is a date (but is really a pitch meeting), she wears this stunning, oh-so-current print, with a dramatic shoulder accent. It’s one of the few times we see her being overtly girly at work since making partner, instead of smart and structured with a feminine flair. So far, Season 7 has been all about the Joan’s funky power suits — complete with lace, bold prints, and big accessories.