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Top 10 Best Mad Men Outfits

I could start this out by saying something cheesy like, “The fashion is really one of the characters in the show”, but let’s just say OUTFITS PRETTY and feast our eyes on some classy, classy ’60s fashion.

10. Betty’s maternity dress.

Love the color and cut. It says, “I’m pregnant but I’m not going to wear a bathrobe everywhere. Also, I’m going to drink. Because I don’t know any better. And I’m a terrible mother. But my hair and make up looks great. Sally, put down that knife.”

9. Don’s skinny tie with suit.

His aviator sunglasses really complete the look. I call this his “I don’t give an eff” outfit, although most of his outfits are “I don’t give an eff” outfits. Because he’s Don Draper, he takes six hour lunches, he doesn’t care.

8. Lane Pryce’s vest ensemble.

Look at this man. Look at him. I just want to tackle him. I want to give him the biggest hug he’s ever experienced. He’s wearing a damn pocket watch!

7. Peggy’s checkered dress.

Finally, Peggy appears in a dress that is not clownish. Sometimes I think the costumer designer hates Elisabeth Moss. But not here. This is a look that says, “I’m a business woman, with business cards.”

4. Joan’s pink dress.

This look is classic Joan: shift dress, pen necklace, updo, bold lips and winged eyeliner. This is the Joan Halloween costume.

5. Sally’s bob.

So fresh, so fashion forward. And she did it herself! This chick is going to be the next big thing. Olsens and Fannings, make way. Kindly.

4. Roger Sterling’s Michael Caine look.

It’s all about the glasses. Original hipster right here. What I love about Roger is that when he wants to look crisp, he’s like a head of lettuce, yo. But I also love when he’s all disheveled from working hard at the office. By which I mean drinking.

3. Don Draper’s Tux.

James Bond, Cary Grant, class, sophistication, greatness. Ignore Betty, she’s just drunk as usual. And he’s all suave about it. He doesn’t even care, he drives a convertible.

2. Betty floral shift dress.

This is my favorite dress in the entire show. It’s bright, fun, classic ’60s and perfectly accessorized. I want this dress. No. I want to be Betty Draper. No. Yes. Sort of. I guess what I’m really saying is that I want to be beautiful and drunk all the time.

1. Betty’s equestrian outfit.

Who else looks like Grace Kelly when they go horseback riding? What is this? I love it. I even see some David Bowie here, circa Thin White Duke. I’m going to start dressing like this every day. I will even carry the helmet. I’ll use it as a purse. It’s got lots of room for lipstick, a wallet and a nice bottle of scotch! Oh Betty, don’t ever change. You’re so the worst that it’s the best!

Honorable mentions:

Trudy’s jeweled dress.

Pete’s smirk gets its own screen credit.

This flight attendant’s uniform.

Who is she? Who cares! Don sure doesn’t. Look at him. He’s high-fiving himself in his head.

Betty’s black dress.

Because Mad Men really needed some comic relief.


What are your favorite Mad Men/’60s looks?

Images from AMC’s official Mad Men site.

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