Do you ever find yourself questioning whether the clothes you’re buying today will still be in style a decade from now? Or do you scroll through old photos of yourself and cringe at the outfits you once thought were cool? Fear not, because in this article, we’re delving into men’s style inspiration from the past and analyzing why certain fashion statements have stood the test of time.

From the likes of James Dean and Bob Dylan to Kid Cudi and Ryan Gosling, we’ve handpicked style icons from each decade and highlighted their most noteworthy looks. By examining the fashion choices of these greats, we hope to shed light on what makes a style truly enduring and how we can incorporate those principles into our own wardrobes.

1950s STYLE ICON | JAMES DEAN

James Dean’s rebellious attitude and preference for functional clothing over the polished suits of his contemporaries made him a true fashion icon. He was among the first to show the world that you can still look stylish and cool without sacrificing comfort and practicality.

One of Dean’s most enduring fashion choices was his preference for plain white or striped T-shirts. At the time, T-shirts were not considered appropriate for normal society and were only worn as undershirts. However, Dean made the humble T-shirt a fashion statement and paired it with his signature lightweight jackets, like the bright red blouson in “Rebel Without a Cause” and the tan suede college jacket.

Dean’s signature leather biker jacket, inspired by his hero Marlon Brando, also became a timeless wardrobe staple that still resonates with men today. His casual, functional clothing choices continue to inspire us to this day. By looking to icons like Dean, we can avoid fleeting fashion trends and focus on classic, enduring looks that never go out of style.

1960s STYLE ICON | BOB DYLAN

Bob Dylan’s 1960s style has had a lasting impact on men’s fashion, with his working man attire of suede trucker jackets, jeans, and rugged boots and refined mod suits providing endless inspiration. Some of his looks are so timeless that they can be almost completely copied and still look great today.

Throughout the decade, Dylan effortlessly transitioned into slimmer, more tailored versions of his earlier outfits, adding dandyish Chelsea boots, black overcoats, and turtlenecks to his wardrobe. These pieces wouldn’t look out of place in a modern-day Saint Laurent ad. His ability to blend casual and tailored pieces is a testament to his status as a style icon.

1970s STYLE ICON | PAUL NEWMAN

Paul Newman’s approach to fashion was understated, timeless, and effortlessly cool. He preferred classic, preppy pieces, often pairing single-breasted jackets with high-waisted trousers or opting for a relaxed look with a button-down shirt and jeans.

Newman’s style was elevated by his use of jackets, which he used to transform his outfits from ordinary to extraordinary. He also had a preference for muted colors and nautical touches, often pairing long-sleeved striped shirts with denim jackets or casual blazers. Newman’s legacy as a style icon continues to inspire men’s fashion, proving that style can be both classic and cool.

1980s STYLE ICON | RICHARD GERE

Richard Gere’s fashion choices in both the ’80s and ’90s were undeniably awesome.  Aside from the well-dressed characters he often played on screen, in his personal life, Gere dressed impeccably.  He often opted for dinner suits with floppy bow ties for his award show appearances, and day-to-day would mix slouchy sport coats with tonal shirts and knits. He also knew how to dress down his suits by going sans necktie and opting for thinner belts.

Gere’s style in the ’80s was heavily influenced by Armani, with his suits featuring a softer, rounder silhouette across the shoulders and fewer buttons at the front. He often combined his pieces in low-contrast ways, pairing black jackets with gray jeans or mushroom-colored button-ups with dark brown tweeds. Gere’s style was effortlessly cool and natural, making tailored clothing look relaxed and approachable. His fashion choices would look just as good today as they did back then, which is not something that can be said for a lot of 80’s fashion!

1990s STYLE ICON | DENZEL WASHINGTON

Denzel Washington was the ultimate 90s style icon. His effortless cool and timeless wardrobe were the epitome of the decade’s fashion. Washington’s wardrobe included staple pieces that remain on-trend to this day: a houndstooth overcoat, a simple black sweater, dark wash jeans with crisp white sneakers. He also rocked leather bombers, suits, and hats – so many hats.

In 1993, Washington’s style was at its peak, and a photo of him exiting LAX in that year, that recently resurfaced and went viral, has become a visual testament to his undeniable coolness. The outfit was a perfect combination of a simple graphic tee, a no-frills baseball cap, easy slip-ons, all-purpose carry-on, and sweet shades. Denzel Washington’s 90s style remains a timeless inspiration that continues to influence men’s fashion today.

2000s STYLE ICON | KID CUDI

Kid Cudi is a multi-platinum selling artist who made a name for himself as a style icon in the early 2000s. He was known for his unique sense of fashion that was ahead of its time and helped establish him as a cultural icon. Despite facing criticism from some in the hip hop community for wearing skinny jeans (before artists like Kanye and others took it mainstream), Kid Cudi remained true to his style and continued to inspire others with his fashion choices.

One of Kid Cudi’s signature looks was his casual streetwear aesthetic, which often featured Air Jordan sneakers, slim fit jeans, simple tees and leather jackets. This effortless yet edgy ensemble captured the attention of fashion enthusiasts around the world and still inspires to this day. For a casual daytime outfit, cop Cudi’s style with a pair of Converse Chuck Taylors, well-fitting jeans, a basic tee, and a biker jacket.

2010s STYLE ICON | RYAN GOSLING

Ryan Gosling is our 2010s style icon that almost wasn’t. After a three-year break from filming in 2007-2010, Gosling emerged on the red carpet scene with a newfound sense of style that was nothing short of radical. He ditched his scraggly beard, bizarre T-shirts, and dirty shoes for a more dapper look, complete with high-fashion Italian suits and tailored looks that rival those of the most stylish men in Hollywood.  He was named TIME magazine’s “Coolest person of the year” and dubbed “The next George Clooney” by the Washington Post.

Gosling’s style is smart, dapper, and undeniably signature. His looks range from smart-casual button-down shirts and classic brown Oxford shoes to tailored suits, sometimes dressed down with a Breton shirt or v-neck tee. For casual looks, he layers a tee with a cardigan and a leather biker jacket. Always with a great watch, but never a flashy one, Gosling has become a modern-day style icon, the embodiment of understated modern cool.