10 Retro Fashion Trends That Have Stuck Around

10 retro trends 2020 hero
Getty Images

Keeping up with fashion trends can be daunting; what was “in” yesterday may not be in tomorrow, and trends once shunned for being outdated can make startling comebacks (fanny packs—we are looking at you). That’s the beauty, and simultaneously the challenge of navigating fashion. 

Fortunately, some pieces have endured style’s many fickle evolutions. 20 and even 30 years ago, runways and red carpets saw many of the same staple pieces that consistently appear today. These ten men show us how the same piece of clothing can be styled to meet the changing times (or to play up the nostalgia).

brad old
Old (1988) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
brad new
New (2019) / Jun Sato/GC Images

Brad Pitt

Trend: White t-shirt

The white tee is a non-negotiable wardrobe staple. It can be dressed up (as seen with Brad Pitt’s leather jacket) or worn for casual traveling. Depending on how you style it, the tee can evoke the nostalgia of decades past and still manage to look modern and fresh. This tried-and-true piece never went out of style, and its appeal lies in its simplicity.

robert old 2
Old (1986) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
robert new 1
New (2017) / Alberto E. Rodriguez/Getty Images

Robert Downey Jr.

Trend: Tinted shades

Robert Downey Jr. has spiced up his shades with this purplish hue for over 30 years. The trend is just funky enough to persist through the decades, and RDJ pulls this nostalgic trend off with charisma and flair.

jayz old 2
Old (1999) / SGranitz/WireImage
jayz new 1
New (2016) / Noel Vasquez/GC Images


Trend: Denim jacket 

Jay-Z’s all-denim ensemble epitomizes '90s style. Far from obsolete, the jean jacket continues to rule streetwear; but as Jay-Z’s two looks demonstrate, the styling choices are nearly endless. Go big and baggy to pay homage to the '90s, or opt for a tighter-fitting jacket (perhaps with a decal or some decorative stitching). This is a piece you can make entirely your own.

lionel old 2
Old (1986) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
lionel new 1
New (2019) / Raymond Hall/GC Images

Lionel Richie

Trend: Leather jacket

Much like Lionel Richie himself, leather jackets are always au courant. They can look elegant or edgy, and they can transition from warm weather to cold temperatures. Richie’s printed leather jacket elevates his runway attire, while his bulkier leather jacket works well in winter. You can choose the topper that matches your vibe and the occasion at hand. 

harrison old 1
Old (1989) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
harrison new 1
New (2016) / JMA/Star Max/GC Images

Harrison Ford

Trend: Blazer and jeans 

Harrison Ford has always been effortlessly cool, and his looks–while understated–have a timeless quality. A blazer and jeans ensemble perfectly satisfies the tricky middle ground between dressed up and dressed down. Ford sports this like a pro.

keanu old 0
Old (1992) / Ron Galella/Ron Galella Collection via Getty Images
keanu new 0
New (2019) / Matt Winkelmeyer/Getty Images

Keanu Reeves

Trend: Combat boots

Keanu’s affinity for combat boots exists today just as strongly as it did in the 90s. No matter how upscale the occasion, Reeves artfully adds combat boots into the mix. Comfortable and durable, the boot completes a rugged, relaxed outfit (and can bring a fancier fit down to earth).

will old
Old (1992) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
will new
New (2017) / Mike Marsland/WireImage

Will Smith

Trend: Turtleneck and jacket

Turtlenecks are far from only practical winter wear. Styled the right way, a turtleneck can make a fit distinctly elegant. Will Smith would know; After 30 years in the industry, he continues to bring fresh looks to the red carpet. He isn’t afraid to play around with prints and textures, and his turtleneck/jacket combo is a perfect example of a man with his finger on the pulse of fashion.

leo old 0
Old (1993) / Barry King/WireImage
leo new 0
New (2019) / Franco Origlia/Getty Images

Leonardo DiCaprio

Trend: Camel jacket 

Leonardo DiCaprio’s career has spanned three decades, and his film characters have had no shortage of memorable and imitable looks. His style has evolved as he’s grown into one of Hollywood’s most sought-after actors, but some staple pieces have remained constant. Camel coats, like those pictured, provide refreshed texture and color to everyday looks. 

jaime old
Old (1999) / Jim Smeal/Ron Galella Collection via Getty Images
jaime new
New (2019) / George Pimentel/Getty Images for TIFF

Jamie Foxx

Trend: Fedora 

Shoes and suits may enjoy more of fashion’s limelight, but don’t forget about hats. Jamie Foxx has donned fedoras on red carpets, exemplifying the eye-catching appeal of this statement piece.

antonio old 0
Old (1995) / Ron Galella, Ltd./Ron Galella Collection via Getty Images
antonio new 0
New (2020) / Michael Loccisano/Getty Images

Antonio Banderas

Trend: Monochromatic fits

Easy and practical, monochromatic fits look coordinated and thoughtful. All-black is a simple classic, and Antonio Banderas shows just how flexible and timeless this look can be. This style continues to grace runways and red carpets today. If you’re looking for a consistent home-run look, this is it.

Did you like this article?
Thumbs Up
Thumbs Down