Skip to main content

Mad Men’s legacy: What ’60s men’s fashion can teach us today

From the conservative '50s to the colorful '70s, here is what we wore in the '60s

Mad Men double breasted
AMC

Every decade is known for something. The 1920s were a time of industrial boom and women’s rights. The 1930s was known for The Great Depression. The 1940s was known for World War II. The 1950s started the Cold War and the Civil Rights Movement. The 1960s saw the boom of counterculture and the Vietnam War. The 1970s began to see the emergence of more social movements like feminism and gay rights. The 1980s were the breaking out point of technology. And the 1990s gave us grunge music and the evolution of the movie industry.

Through all of those decades, fashion evolved along with us. And the ’60s fashion men clung to holds a special place in the history of our evolving aesthetic. Gone were the days of the ’50s conservative looks, and we weren’t quite at the colorful, wild styles of the ’70s yet. What we saw in the 1960s was a period of transition. And we may be there again in 2025.

Recommended Videos

Mad Men is a series that focuses on the decade through the eyes of the Ad Men of the day. But you can look at the styles of the leading men in the show to see them embody the growth of the fashion scene we may be looking forward to again in the coming years.

Fashion evolved with us through tumultuous growth

Don and Roger from Mad Men
AMC

What comes to mind when you think about the 1960s? On the positive side of the board, you can point to the Civil Rights Movement and our quest for racial equality. You can point to counterculture and the music that inspired it from names like Bob Dylan, The Beatles, and The Rolling Stones. Then there was the flip side of the coin, essentially things that caused the need for all the above.

It was a decade defined by war as we fought a Cold War against Russia and an all-out war in Vietnam. Both of these events led to a cultural war here at home. Assassinations of Dr. Martin Luther King Jr. and the Kennedy Brothers made it feel like we were on the blink 24 hours a day. But we made it to the 1970s and evolved into something new. Men’s fashion was there with us the whole way.

We watched as men began in the subtle blues, grays, and charcoals popular in the 1950s and advanced to brighter colors and more outlandish patterns. We saw the ditching of simple black wingtips as the only acceptable choice for office footwear and the acceptance of the brown oxford shoes. We saw the basic skinny tie start dying out as men looked for something more lively. And finally, we eventually left the fedora in the rearview and started growing out our hair.

As society changed, so did our style with it. Now, we see vintage styles coming back, which may symbolize our societal desire to evolve again into something more. Here is how you can look to the Ad Men of the ’60s-based show Mad Men to guide you through the growth.

The style of Don Draper

Don Draper smoking a cigarette
AMC

Few people would argue that Don Draper (Jon Hamm) is the main character of Mad Men. He is the debonair genius at the center of the ad agency, and we see him present as a man in control of everything. He is the envy of those around him, and he plays the part well. Even if we don’t always see it as a viewer, we know there are cracks in the facade, and he covers them up in suits, alcohol, and cigarettes, finding his way to the next victory in the boardroom. The last seems like the only thing that gives him meaning in life. Even though he says it doesn’t exist.

Looking at how he is dressed, he is the man’s man. He is the symbol of what the country grew from. Strong lines, masculine colors, and a traditional style that never bends to fads. He uses the blues, grays, and charcoals like a uniform. In 2025, you will see a return to these colors and the vintage aesthetic we look back on fondly. If you’re hoping to nail the 1960s fashion look, Draper is the inspiration for you. Stay subtle and low-key, and keep your color palette muted for 2025.

The style of Roger Sterling

Roger Sterling and Don Draper on plane
AMC

Next, we have Roger Sterling (John Slattery). In many ways, he is Don’s opposite. The two seemed to be paired together from the beginning, a little bit of yin and yang to make them more complete. Where Draper is a serious professional, Sterling enters every room with a sarcastic jab at someone or a quippy remark to bring levity or sometimes a tragic reality to the current moment. And for someone who doesn’t take himself as seriously, there is an opposite sartorial aspect to him.

Where Don is primarily seen in the traditional dress of a businessman, Roger may see that as a representation of his father (the real Sterling with his name on the door). As a way of rebelling and accommodating that Madison Avenue-sized chip on his shoulder, you see him clad in some of the brightest colors and flashiest patterns of any of the men surrounding him. He always stands out. And he does it in stylish ways. He doesn’t just go with a navy suit; he adopts a pinstriped suit. He doesn’t wear simple solids; he goes with a double-breasted blazer and plaid pants. He drops the necktie and wears a neckerchief.

If you want to be the Roger Sterling of your group, focus on grabbing louder pieces to work into your wardrobe. Pair your solids with patterned pants or jazz up your outfit with a bright-colored pocket square. Our suggestion is definitely to adopt the neckerchief.

Pete Campbell

Pete Campbell in a burgundy blazer
AMC

Finally, we come to Pete Campbell (Vincent Kartheiser). Most people who know this character see him as the weak antagonist always out for number one. And while that is true, he is also simply looking for a place to belong. He begins the series looking for respect and goes about getting it in all the wrong ways. Throughout the seasons, he grows into becoming his own man and finds respect where it belongs by giving it to others.

Stylistically, he is who many of us are. He is somewhere in between Draper and Sterling. At the beginning of his arc, he seems to be emulating Draper’s look, but all his suits and looks are ill-fitting. He then comes into his own and branches out with more color and flare, all while filling his suits out more appropriately. This is who we all tend to be. Don Draper is a classic style with a dash of trend. Roger Sterling is trendy with a dash of class. Pete Campbell is the guy who found the healthy mix between them and does both equally well.

The 1960s were marred by war abroad and violence at home, but were seen through music promoting peace and civil discourse that paved the way for a better version of who we were. The love of ’60s style and the adoption of the vintage aesthetic may be a subconscious connection to the same feelings. Sartorially setting ourselves up for tumultuous growth into something better and brighter on the other side.

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
Travel like a secret agent with 5.11’s industry defining Founder’s Jacket
Always Be Ready even when dressed for the boardroom
5.11 Founders Jacket

We have all seen James Bond travel the world and carry out missions of the utmost importance while looking stylish as Hell. The one thing that should baffle anyone in the clothing or travel industry is how he did it with not a wrinkle in sight. Of course, there are all kinds of tricks for you to get to your destination and take care of wrinkles. But then there is another problem: how do you look amazing while having everything you need? The experts in the mindset of Always Be Ready remedied both problems with the drop of the 5.11 Founder's Jacket. While it will be your best friend in everyday carry preparedness, it doesn't sacrifice the style you need either.

The jacket has been a pet project of co-founder, former CEO, and current Executive Chairman Francisco J. Morales, for years. “As someone who has been deeply involved in the design and innovation process throughout my years at 5.11, the release of the 5.11 Founder’s Jacket is incredibly special. It represents the culmination of our dedication to crafting quality gear but also tells the story of our brand's journey. I'm excited to share it with our community of professionals and enthusiasts who inspire everything we do as a brand.”
Perfect for the man on the go

Read more
I wore Men’s Wearhouse every day for a week — here’s what I discovered
Here are my thoughts on one of the biggest menswear destinations on the market
Man in Men's Wearhouse Blue Suit

I have always been a guy that loved a good suit. As a matter of fact, at one point, I was only comfortable in suits, and I had to get out of my comfort zone to elevate my streetwear and casual looks. I recognize that is the opposite of most people; welcome to my world. Virtually everything I do is the opposite of the rest of the population. So, when I needed to buy a new suit, I started researching, and one place kept coming up in the recommendations and the Google searches: Men's Wearhouse. I wanted something upscale, something with a little more punch. And if I am being honest, I always felt like Men's Wearhouse was that place you went to if you needed to rent a tux for prom or a wedding or if you needed a suit really quick. But now that I have spent over a decade in the industry, I gave it another chance and decided to wear the brand every day for a week to discover once and for all if Men's Wearhouse is worth it.
Tailored clothing

When considering , you almost always go right to their tailored offerings. Of course, as a man who loves suits, I love to wear them as often as possible, so I am going to wear a suit or some kind of tailored garment every day to work. Something about them simply makes me feel better. Here is how they looked during my week.
Custom Monday

Read more
5 ’80s men’s fashion trends that are making a comeback
Revitalize these 80s trends for today's style
80s men fashion couple

Big hair, bright colors, hair bands, and some of the greatest movies ever made; the 1980s were a great time. Nostalgia plays a big role in our lives. Any time you start doom-scrolling social media, you are hit with everything from AI videos reimagining the time of our childhoods, younger people discovering Guns N Roses for the first time, and the reviews of a Back to the Future rewatch. Of course, every decade has its version of the same telling aspects like music, movies, and culture, but there is one aspect of every decade that sets it apart from every other quickly: fashion. Men's fashion in the 80s was known for acid-wash jeans, neon colors, and cropped shirts. But as with every decade, there are trends that come back, and you should be ready to revisit old times with these 80s men's fashion trends that are making a comeback.

I am a huge fan of a good comeback trend, and Will Giddon, director of brand at Rothmans NYC, shares the sentiment and loves some of the trends he sees on the comeback trail. "I love that the fashion of the 1980s is making a comeback in modern men's wardrobes. It adds a bit of a nostalgia factor and gives some extra personality to the way men are dressing."

Read more