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.
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
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
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
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
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.
