The Most Stylish Men From Every Decade

by Friday, March 18, 2022

Ever wondered who debuted the double breasted jacket or the beautifully quiffed hair?

Throughout the last 75 years of men’s fashion, there have been a good selection of sharp young gentlemen, and some that just didn’t make the cut. We’re taking a look back at the most stylish men of every decade who helped pave the way for men’s fashion today.

Browse through our picks of the most well-dressed men from the 50’s on.

The Most Fashionable Men in History

1950’s: James Dean and Elvis Presley

No decade saw perfectly tailored suits quite like the 50’s. Male style icons during this time had custom-fitted suits that were so distinguished, they wore to multiple events (something you rarely see happen today). Grooming was a staple during this time – you hardly ever saw messy hair or an unclean shave. More conservative dressers such as Frank Sinatra and Miles Davis made waves, but we give this decade to James Dean and Elvis Presley. These younger studs took more risks, adding color and the legendary quiff into the mix.

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1960’s: Steve McQueen

The immediate thought people have when they think of the 60’s is long hair and bell bottom jeans. Men in the 60’s either kept their posh, tailored look or went wild. We see guys today draw inspiration from both. The free-spirit bohemian Jimi Hendrix as well as the Don Draper-esque gentlemen.

We had to give it to Steve McQueen. You simply can’t understate the influence McQueen had on men’s fashion. Companies proudly displayed his name on products simply to give them credibility. His style is timeless and seen all over the fashion arena today.

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1970’s: Robert Redford and Elton John

One word to describe the 70’s: adventurous. While we saw bits of color come into play in previous decades, men finally embraced all out crazy styles during this decade. People stepped further away from structured, tailored suits and got ballsy with colors, patterns, and different trends. Think velvet suits with a ton of chest hair.

Elton John certainly embraced the wackiness of this decade, with animal print outfits, a gapingly exposed chest, and colorful sunglasses while Redford experimented with a bit of a more toned-down style during this time.

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1980’s: David Bowie

The 80’s have a bit of bad rep when it comes to fashion, and we’ll blame that on the gold spandex hysteria. However, there were certain standouts that held true to solid men’s fashion. They generally went with a tailored look that’s a bit looser than what we see today.

David Bowie not only had groundbreaking records, but groundbreaking style as well. He certainly dabbled in crazy colors, but he always looked incredible in a tux and well put-together, on stage or not.

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1990’s: Johnny Depp

Though style didn’t seem on-point in the 90’s either, we’re seeing bits and pieces make a comeback today. I certainly hope wide-leg pants and oversized hoodies don’t make a resurgence anytime soon, though there were some notably well-dressed men during this decade that we shouldn’t overlook.

Johnny Depp did the bad-boy thing right. He understood classic style and played upon it. Tousled locks, statement blazers, and lots of leather did him justice. Not to mention, Kate Moss on his arm didn’t hurt.

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2000’s: David Gandy

This decade brought back the slimmed-down look. Men went for more tailored suitsand even re-introduced ankle skimming trousers into the mix. We saw an increase in slimmer fitting jeans, thanks in part to stylish indie bands like the Arctic Monkeys. But the biggest influence was the rise of the male supermodel. The menswear movement really took off, and it was finally a topic discussed mainstream.

In 2006, David Gandy walked the Dolce & Gabbana fashion show and took the men’s fashion world by storm. Anything he wears, from a tailored suit to a leather jacket, looks incredibly sharp.

Today: Eddie Redmayne and David Beckham

Today, it’s all about confidence and originality. We see pieces from every decade in men’s fashion. From lifestyle sneakers, to slim-tailored suits, men’s style is more talked about than ever before.

Do you agree with our picks? Do you have other icons in mind? Share your thoughts with us below and don’t forget to like us on Facebook!

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Originally posted on January 21, 2016 @ 2:40 AM



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