Mad Men: Don Draper’s 5 Most Dapper Outfits (& 5 That Were Shabby)

There is nothing quite like fashion from the 1960s. Women wore dresses all the time, and men wore suits every day to work. There was a suit for every occasion. These fashion trends are presented in the drama series Mad Men.

While every character looked glamorous on the show, Don Draper (Jon Hamm) helped reinvent the classic 1960’s look: Sleek gray suits, skinny ties, and many fedora hats. He’s the man to admire on the show and he had many iconic outfits throughout the show’s seven seasons. However, some of his outfits weren’t as dapper as the others. Take a look at Don Draper’s best and worst outfits from the show.

10 Dapper: Classic White Dinner Jacket

Don Draper is known as a womanizing advertising executive. He’s good at stealing looks and, well, other people’s wives. It’s hard not to resist his classic charm, including when he wears his signature white dinner jacket.

White is a bold color choice for anyone, but Don pulls it off in the show’s season two episode, “The Gold Violin.” He looks sleek, modern, and ever so sophisticated. The jacket has one button in the front, an open breast pocket, and two hip pockets with straight flaps. Don decides to wear a white formal shirt underneath the dinner jacket and he pairs the outfit with black trousers. A thin black bow tie completes the classic look.

9 Shabby: Cream Silk Suit

Don Draper was always handsome. No one is arguing about that, but sometimes, his outfits were simply “okay.” For example, in the season six episode “A Tale of Two Cities,” he wears a cream silk suit while experimenting with hashish. Don and Roger Sterling (John Slattery) attend a hip party in Hollywood, but Don’s suit isn’t as impressive as his other fashion choices.

The cream silk sports coat and Angelico-made gray pants don’t necessarily match. The outfit also includes a white long-sleeve button-up dress shirt, a wider brown and turquoise tie (contrasting Don’t typical skinny straight ties), and silver-colored cufflinks with four triangles. The outfit doesn’t seem complete.

8 Dapper: Fedora Hats

In the 1960s, men wore hats everywhere. So, Don Draper wears hats on numerous occasions. He wears different fedoras — a classic look for the ‘60s. All of his hats are made from good felt and they have a similar shape. The shape of the hat perfectly accentuates Hamm’s solid, straight-sided face.

The fedora hats will always be associated with the ‘60s. Now, thanks to Mad Men, they will also be associated with Don Draper. He always looked best when his outfit was completed with a fedora hat.

7 Shabby: Mock Turtleneck

By the show’s sixth season, Don Draper caught up to the revolutionizing trends of the 1960s, including this mock turtleneck suit. However, it’s a different look than what most people would expect from the character.

Don wears the outfit in the season six episode “The Quality of Mercy,” as well as other occasions. While the black cashmere turtleneck might complement his dark green plaid sports coat, the turtleneck resembles athletic performance material, which clashes with Don’s character. He still looks presentable in the outfit, but it’s not his signature look.

6 Dapper: Polished, Conservative Suits

During the show’s third season, Don deals with the collapse of his marriage to Betty (January Jones). One would think his fashion would reflect his turmoil, but that’s not the case at all. Instead, Don still wears sharp, conservative suits to keep his polished façade.

The only thing that changes this season is Don’s ties. He experiments with stripes, polka dots, various shapes, and more. The ties complement his polished attire. If you were just looking at Don, you had no idea he was going through a divorce.

5 Shabby: Checkered-Jacket Suit

The show’s fourth season brought back some of Don’s signature looks, including the skinny ties, white dress shirts, etc. However, when he goes on a trip to California, he decides to wear a checkered-jacket suit. It was an experiment, but it didn’t have the best results.

Don has worn plaid suits and varying styles before, but this style choice doesn’t quite cut it. He pairs it with a gray fedora. The outfit’s varying styles clash, and viewers are left wondering what happened to Don’s typical appearance. This isn’t the Don Draper everyone knows.

4 Dapper: Classic Plaid Sportscoat

Plaid suits either work or not. For Don Draper, it worked in the season five episode “Signal 30.” Viewers were shocked when Don arrived at a dinner party wearing a daring plaid sportscoat. It’s completely different than his typical attire, but his new wife, Megan (Jessica Pare), bought it for him, so he was going to wear it.

In the 1960s, plaid sportscoats were popular fashion choices for men as they began to transition out of the traditional suits and ties from the ‘50s. Mad Men costume designer Janie Bryant commented, “It’s definitely out of his usual (style). It’s a louder palette, younger and fresher.”

The sportscoat didn’t sit well with every viewer, but now it’s a classic, iconic look from the show.

3 Shabby: A Less-Successful Plaid Jacket

Don Draper continued to experiment with his fashion in the show’s final season. The show’s timeline ends in 1970 and it seems Don was ready to get “groovy” with this less-successful plaid jacket from “The Runaways.” Megan hosts a fancy house party for her acting friends, so Don wears this plaid jacket with a white dress shirt.

He sticks out at the party. While Don is the main character of the show, he shouldn’t be this noticeable. Hopefully, he learned his lesson that not every plaid jacket works.

2 Dapper: Sharp, Classic Suits

When someone thinks of Don Draper, they imagine him wearing a sharp, sleek suit with a crisp white dress shirt. This is the classic men’s suit that popularized in the 1950s. It’s soft and thick in the shoulders and chest, but then it tapers down at the waist, giving him a V-shaped silhouette that everyone loves.

Don’s suits are made from threads of colors to give the impression of one unified color. In addition, Don often pairs the suits with a skinny black tie. Don tried different styles of clothes during the show’s seven years, but he kept coming back to this signature look. Can anyone really blame him?

1 Shabby: The Hawaiian Sports Jacket

The show’s sixth season two-part premiere, “The Doorway,” takes Don and Megan to Hawaii for a business trip. Don decides to let go of his usual fashion sense and wear casual, Hawaiian attire. Did anyone ever think they would see Don wear a blue and white floral Hawaiian shirt?

The episode includes a surprise wedding, in which Don meets a young Army man who needs someone to give away his bride. Don volunteers for the role, and he wears a light green/mustard-colored sports jacket to the wedding. The jacket resembles Don’s typical style of formal attire, but the color isn’t very flattering. Let’s hope he didn’t bring it home to Manhattan with him.

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