50 of the best outfits from 'Mad Men'

May 2024 · 13 minute read

"Mad Men" is considered by many to be one of the shows that ushered in a golden age of television – in no small part due to the impeccable production design and wardrobe. During its seven-season run, "Mad Men" was known for always putting characters in costumes that were period-appropriate but also timeless and fashionable even to modern viewers.

We've rounded up some of the best, most memorable outfits from the show's history.

Rachel Menken makes an entrance with a feathered hat in 1.3.

This hat makes an impression. AMC

Her bright pink look with a bold hat is stylish and put together, perfect for when she puts the Sterling Cooper boys in their place after not putting in the research for her account.

Helen Bishop, the new divorcee on the block, threatens the local housewives in her sharp weekend look in 1.3.

Bishop's outfit is stylish and makes a statement. AMC

Her fiery red hair is complemented by the red in her button-down shirt and trousers — a modern look that stands apart from the neighbor moms' floral dresses.

Roger Sterling's look is consistent, but flawless.

Sterling Cooper's look is iconic and timeless. AMC

The head man-child of Sterling Cooper (Draper Pryce, etc.) rarely deviates from his formula of a neat, dark-colored three-piece suit, such as when he delivers his famous “why we drink” monologue in 1.4. And why would he? 

Betty is a vision in white, even when stumbling home with Don after an award ceremony in 1.5.

Betty pulls off this all-white look. AMC

The statuesque cut, the glittery bodice, and jewelry, the long white gloves — the look is flawless, not at all diminished by the slight end-of-the-night looseness to her hair.

We would be remiss not to celebrate Don's classic work look.

Don Draper can work the neutral looks. AMC

The narrow tie, crisp white shirt, and suit in any number of neutrals – like this cool grey in 1.5 — it's the famous Don Draper look for a reason.

You didn't miss Joan, did you?

Joan was never afraid of wearing a bold color. AMC

Thought not. Joan, always a stunner, is prone to wearing tighter dresses, often in bold colors like this red number in 1.6.

Trudy always looks the part of a Manhattan heiress.

Trudy is always dressed to impress. AMC

She may be young, but she's always dressed like old money — case in point, this delicate white polka dot set with a netted hat to hold her updo in 1.8.

Betty's cold-weather looks are a layering dream.

Betty also pulls off this casual look. AMC

This wide-collared blue coat with a neatly-laid scarf is accented by a cute but mature-looking black headband — an incredibly put-together look that contrasts wonderfully with the strange, emotionally frayed scene where she confides in neighbor kid Glen in 1.13.

When Betty and Don go out on the town, she keeps a surprise underneath.

Betty's lingerie is a surprise for her character. AMC

She takes off her delicate champagne-colored dress to reveal sexy black lingerie in 2.1. It's a little risque for Betty, and she seems proud of herself for taking the risk.

Kurt Smith's giant knit turtleneck sweater signals that he is far from another suit.

Kurt Smith's sweater does not fit into world of Sterling Cooper but it works. AMC

The German wunderkind of ad creative shows up at Sterling Cooper in 2.1 in this chunky knit number that couldn't be farther from the Madison Avenue look — and gets the job. His Beat sensibility is actually his strength.

Pete's blue suits are a character trademark.

Pete's blue suits are actually a way to stand out. AMC

His corporate style is generally very reserved, but the blue suits he wears, like in 2.2, are a subtle way of standing out.

Don's off-duty outfit is a standout.

Apparently Don Draper's at home look is more preppy. AMC

This sweater he wears at home in 2.3 is cozy and preppy, a strong counterpoint to Betty's traditional equestrian getup.

Bobbie Barrett, wife of insult comedian Jimmy Barrett, makes a strong entrance in red.

Red is a confidence color. AMC

The bold red coat with fur trim and a matching hat signify her confidence and power when we meet her in 2.3.

Betty's tennis outfit is more fashion than it is function.

Betty is the definition of preppy in this tennis outfit. AMC

The white headband and pleated white dress — with that little tennis racket decal — is the perfect preppy look for her country club visit in 2.6.

Betty going-out look couldn't be more perfect.

Betty's dress is the perfect mix of blue and diamonds. AMC

In 2.7, Betty wears a gorgeous, brightly saturated blue gown with long, sparkling earrings. 

Peggy's style starts to show gradually as the series progresses.

Peggy's outfits change by the second season. AMC

Her modest means and lack of fashion-savvy dictate Peggy's frumpy style when she's a wide-eyed newer employee at Sterling Cooper, but slowly, she introduces bold patterns and tailored pieces to her wardrobe – like this black and white checked dress with an interesting wide collar in 2.10.

Betty makes maternity fashionable.

Betty knows how to make maternity looks shine. AMC

As baby #3 nears full term, Betty looks fresh and put-together as ever in this embroidered pink dress with a fun collar in 3.2.

Jane Sterling shows off to her former coworkers in a flashy outfit.

Jane makes a black and white outfit flashy. AMC

Jane's work outfits were always pretty and flattering, but when she shows up at Sterling Cooper in 3.3 with a gloating expression on her face, she drives the point home in a black-and-white diamond dress and big matching hat.

Betty looks downright angelic in white lace and pale pink accents.

Betty's lace outfit is perfect for a Kentucky Derby party. AMC

At Roger's Kentucky Derby party in 3.3, Betty forgoes the church hat and opts instead for this simple but very pretty lace number — still making pregnancy look glamorous.

Harry Crane's seersucker suit is another southern-inspired standout.

Harry Crane also dresses for the occasion. AMC

At the same party that episode, Harry Crane shows up in a full seersucker suit, which he had probably just been dying for the chance to wear.

Lane's expat style is buttoned-up, but with some visual interest.

Lane is always dressed to the 9s. AMC

Like Roger, Lane goes for three-piece suits virtually every time we see him at work. However, the fit tends to be a bit more relaxed, and he often plays with unexpected color pairings — like this light grey vest and striped tie with a classic black jacket and pants in 3.5.

Joan's cobalt suit dress is a classic.

Joan is killing it again with a well fitted bold colored look. AMC

Bold color + exceptional fit = a surefire Joan Holloway stunner. This blue dress, worn in 3.6 with little white driving gloves and her staple accessory, a pencil necklace, is one of many such winners.

Peggy moves into the spotlight as she becomes more sure of herself at work.

As Peggy gets more confident, so does her style. AMC

By this point a fixture of the creative team — and at the beginning of a relationship with Duck — Peggy's growing confidence shows as she works more color into her workplace wardrobe, like this belted red sweater vest layered over this delicately printed silk blouse with a pleated skirt in 3.7.

Betty wears her famous European mod look for a night in Rome.

Betty goes all out in Italy. AMC

On top of finally getting to show off her Italian skills, she goes all out in 3.8 with a swingy, strappy black dress with big, dangly pearl earrings and a tall, playful updo.

Roger's triple pocket square adds a fun touch.

Roger does what he can to get creative with his outfits. AMC

The men of Madison Avenue only have so much room to play around within the corporate dress code, but this kind of detail makes a grey suit like Roger's in 3.11 more interesting.

By the beginning of season four, Peggy's practically a style icon.

By season four, Peggy is a fashion icon. AMC

Having now jumped ship and been part of the formation of SCDP, Peggy's finally dressing like the career woman she is. In 4.1 she shows off some new, well-fitting pieces that feature more color, like this blue jumper layered over a printed blouse with a big bow at the neck.

At the SCDP Christmas party, Joan is wrapped in red.

Joan stuns in the perfect Christmas outfit. AMC

Showing off in a tailored dress as always, Joan celebrates the season in 4.2 with a red dress that features a little bow at the neckline and a big bow in the back – and a little sparkly barrette in her updo.

Pete's seasonal garb is worth mentioning, too.

Pete also rocks a festive look. AMC

His burgundy jacket in this episode is a fun touch, fitting for a Christmas party.

Jane's sparkly snowy dress is stunning.

Jane gave yet another great take on a holiday outfit. AMC

The SCDP Christmas party was a big fashion moment. Jane, always a glamourpuss, sports a fitted white dress with a big, gorgeous sparkly collar and dangly pearl earrings.

Don tries some color when he travels to California.

Don lives it up in California with this yellow outfit. AMC

In 4.3, while visiting an old friend (and secret-keeper) Anna Draper, Don wears a pale yellow checkered jacket. The Golden State is good for his wardrobe, it seems.

Megan slowly emerges from the secretarial pit with bright colors.

Megan stands out in this suit. AMC

She never exactly blended into the woodwork, but outfits like this breezy mint suit in 4.9 put Megan closer and closer to the forefront of our — and Don's — attention.

Stan's polos are aggressively casual, compared to the rest of SCDP.

Stan's outfits are noticeably casual. AMC

It's fitting, given that Stan works in creative, but he rarely dresses even almost as formally as the other men in the office — case in point, this colorful, candy-striped polo he wears in 4.11.

Peggy's demure blue dress with a single strand of pearls means business.

Peggy's style continues to get better as the seasons go on. AMC

This simple dress with red pleats and a pearl necklace speaks to her upward mobility and growing self-possession — she fends off Stan's moves without hesitation in 4.11.

Megan wears a swingy mod number for her sexy performance of "Zou Bisou Bisou."

Megan's performance and outfit is iconic. AMC

Her song and dance scandalize Don and his coworkers in 5.1, in no small part due to the tiny black dress with wide chiffon sleeves.

Michael Ginsberg's interview outfit is (perhaps tellingly) offbeat.

Ginsberg's outfit is definitely making a statement. AMC

After Stan, Michael is the second creative hire to stay far away from grey suits. He shows up to interview with Peggy in 5.2 wearing a turquoise and pink plaid jacket, a clashing tie, a printed shirt, and jeans. Bold move, Ginsberg.

Peggy's green sleeveless dress with a red bow is cute but grown-up.

Peggy wears an outfit that is cute and mature. AMC

The jewel tones here, in 5.2, look mature and fashionable, balancing out the bow and collar.

Joan welcomes Greg home in a rose-patterned black dress.

Joan dresses to impress when Greg comes home for the war. AMC

When her husband Greg returns from war in 5.3, Joan greets him in a black dress covered in roses, and her hair styled in loose curls. 

Don wears a black, red, and white plaid jacket to an after-hours get-together.

Plaid was definitely the theme of the evening but Don's stands out the most. AMC

A suit jacket, but make it for the weekend — Don hardly dresses down for casual Saturday events, he just adds some color, like this jacket he wears in 5.4.

Jane exposes her midriff in a glamorous white dress.

Jane's outfit is amazing. AMC

Roger and Jane may have begun resenting each other already, but she's clearly not resenting the money that comes with her lifestyle — in 5.5., as usual, she's dressed to the nines in a daring, belly-exposing high-necked dress with dramatic earrings and pearls in her hair.

Megan dresses like a bowl of sherbet to visit pastel-paneled Howard Johnson's upstate.

Megan's outfit is the perfect look for a vacation. AMC

Unfortunately, the orange sherbet isn't her thing and it launches the Drapers into a dramatic tiff in 5.5. Still, the coral-colored ensemble with a chevron-patterned jacket and big sunglasses with printed frames just scream “weekend getaway.”

Joan shows us how to do monochromatic.

Joan's portrait day outfit is perfect. AMC

In 6.1 she wears a purple dress over a slightly lighter purple ruffled blouse, with a big gold brooch. Is there anything she can't pull off?

Megan looks gorgeous as always in a sparkly champagne-colored dress at dinner.

Meghan knows how to dress up. AMC

When her mother comes to visit in 6.5, Megan dresses up in head-to-toe glitter with this dramatic collared dress and statement earrings.

Peggy's navy and white suit dress is daring and fun.

Peggy is taking advantage of the option for patterns. AMC

In 6.6, Peggy wears this double-breasted suit dress with a patterned skirt. The dress code seems to be getting more fun around the office, even for all-business Peggy.

Joan's nautical outfit looks breezy and natural.

Joan always knows how to dress the part. AMC

While all of the agency starts looking west, Joan's outfit gives us distinctly east coast vibes with her anchor-embroidered sweater vest and patterned hair scarf.

Peggy's pantsuit rocked viewers.

Peggy's first pant look wowed viewers. AMC

Her red and black checked pantsuit in 6.12 had viewers talking. For Peggy, until now a skirt devotee, the pants seemed to represent a final pull away from traditional femininity.

Megan grabs Hollywood by the horns in her airy blue look.

Megan kills California style. AMC

The powder blue chiffon dress, with matching winged eyeshadow and big gold earrings, are what Megan wears as she steps into the hot California air in 7.1, ready to take her dreams seriously.

Betty looks prim and proper, if irritated, in a pink suit set and black sunglasses.

Betty looks amazing, even though she is annoyed. AMC

When she comes along as a chaperone on Bobby's field trip in 7.3, she looks uncomfortable, but as put together as always.

Peggy's all mod in red and pink.

Peggy's outfits keep getting more creative. AMC

The progression of time is showing, as Peggy wears this fun color pairing and a set of white hoop earrings to work in 7.6.

Peggy gets us again in Ray-Bans and a striped shirt.

This outfit really shows how much Peggy has changed and grown as a person. AMC

Who would have known Peggy's style would come so far? When she shows up to her first day at the big agency in 6.13, hungover and oozing confidence, she's wearing bold stripes and managing her hangover with a pair of sunglasses.

The last we see of Don Draper is a loose, white cotton shirt blowing in the breeze.

This is the last outfit we see Don in. AMC

In the show's (not so) ambiguous ending, we see Don in a look that echoes his regular work button-downs, just in a slightly more casual fit and fabric. Don may not know who he is anymore, but all it takes is a look to know that some things never change.

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