Dress Like Mad Men’s Don Draper | 1960s Fashion

Oscar and I- Mad Men Style

Ever since we started watching AMC’s Mad Men, my husband and I have been falling love with early ’60s fashions. Oscar especially likes Don Draper’s style. It’s clean, simple, and classic with a twist of sexy – just like my man. When it came time to decide what to wear for his company’s holiday party, picking the Mad Men style was easy. Surprisingly, finding a Don Draper Style outfit wasn’t too hard either. Here is how it came together and how you can find your own Mad Men suit.

The Mad Men of New York in Conservative Mid ’60s Suits

The Mad Men Suit Jacket: My quick internet research of 1960s men’s fashion showed me that suit jackets were known for having very narrow lapels. Unlike Roger Sterling, who wears wide peak lapels (popular in the 1940s and appropriate for his age), lapels were usually no more than 3 inches wide. They had small notches and sometimes had a rounded rather than sharp point. The other defining suit style was the pockets. They had either square flaps with rounded corners or no pocket flaps at all. Finally, the jackets only had two or three buttons on a single-breasted suit. In the late 60s, the buttons dropped down to only one.

Tip: If you find a jacket with pockets, just tuck them inside and you’ll have the slit pocket look instead. See the photo above.

Mad Men Grey Suits with Skinny Ties

We really lucked out on finding an original early 60s grey suit jacket for $12 at the very first thrift store we looked. The grey was a subtle grainy blend of grey and black threads. The jacket didn’t have matching pants so that became the next thing to find. Shop here for 1960s style men’s suits.

Dancing in a Thrifted 1960s Suit Jacket and Modern Slacks

Another option is to wear a sport coat in a different pattern or color than the dress pants. These became very common in the mid to late ’60s. See these from Mad Men season 6. Navy blue, ivory, tan, rose pink, mustard yellow, sage green, and baby blue were just a few of the colorful options. Big plaids, checks, herringbone, vertical stripes and pinstripes were also available patterns. Pair dark sport coats with lighter solid color pants or vice versa, light sport coats with dark pants. You can also add a brightly colored vest (red, yellow) or patterned vest (plaid, windowpane) under a solid suit or sport coat.

Late ’60s Sport Coats

The Mad Men Suit Pants: Early 1960s pants were flat fronted and high on the waist. No pleats! They were straight with the occasional slight taper, no cuffs, and stopped right at the ankle or about 1 inch above the rim of your shoes. Most men’s dress pants today are modeled after ’60s styles, so your chance of finding good pants wherever you normally shop is very good. I would avoid the supper skinny fit or anything with a very low waistline. Look for “classic” or “slim” fits. Shop here for men’s 60s style pants and trousers.

Thrift stores didn’t give me the color of pants I needed to match the suit jacket, but my local departmental store, Kohls, did. Since pants do not come in multiple lengths, I simply bought a pair that was one to two inches shorter than what Oscar normally wears. The length turned out perfect.

1960 Men’s Suit Outfit

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The Mad Men Dress Shirt: A basic white button down shirt with pointed collar. These haven’t changed much in many decades, except for the cuffs. You may remember Don Draper taking on and off his cuff links a lot in the show. Cuff links were an everyday accessory with men’s shirts. Today’s work dress shirts don’t have the proper cuffs and holes for cuff links. You will need to get a French cuff white shirt instead of a modern dress shirt. In a pinch, you can just punch some holes in a regular dress shirt, but this doesn’t work as well because the shirt cuffs won’t hang out beyond the jacket sleeves as they should. Invest in a good French cuff shirt and a nice pair of cuff-links and you’ll feel very sophisticated in them.

1950s -1960s Nerd / Scientist Short Sleeved Shirt, Skinny Tie, and Tie Clip

The Mad Men Tie: I really love ’60s ties. They were so thin and narrow. This fad has been back fashion for a few years.  Ties were about 3 inches wide in either solid colors or fun thick stripes, plaids, or textured weaves.  Shop here for men’s 60s ties here.

1964 Skinny Ties Catalog Ad

The Mad Men Shoes: Shoes are another item that hasn’t changed much over the last 60 years. A basic pair of shiny black or brown lace-up Oxfords or slip-on loafers will work well. The wingtip Oxford is a more decorated style of shoe and equally common for businessmen. Monk strap shoes were fashionable with the trendier mod men. Shop men’s 60s shoes.

1960s Style Men’s Shoes

The Mad Men Hat: No men’s 1960s outfit would be complete without a Fedora hat. These hats have been popular since the 1920s, which is why everyone in Mad Men man wears one. Hats usually matched the suit. Brims were wide, with 2 inches being the most common. The larger your head, the wider the brim should be — small brims for smaller heads, etc. The one Oscar has is the Jaxon Pinch Crown which is a very nice and affordable Fedora. Shop 1960s men’s hats.

And that completes our Don Draper Mad Men outfit guide. You can make an outfit for yourself by looking for clothing that I have described above from your local thrift stores, department stores, or online stores.

Here are some ore outfits we have worn for a late 50s or early 60s event:

Oscar and I in our Vintage Mad Men Clothing

Another Party, Same Suit

Oscar Wears a 1940s suit (Roger Sterling style) and I’m in a Vintage 1950s Dress

Casual 1950s/60s outfits, Real Vintage

Learn More about 1960s Men’s Fashion Here