A look back at the Rocky star’s knockout style from the ‘70s to today.
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Before Michael B Jordan shocked us in a leather harness, Shawn Mendes dared to bare in sheer shirting, and Jason Momoa committed to think pink, Sylvester Stallone broke all the red carpet rules, opting for bold modern style over the traditional garb worn by Hollywood’s leading men. Like any Stallone film, his style was far from boring. Standout gold accessories, unconventional textural mash ups, lots o’ skin, and seriously fresh kicks—the Rambo star could, and did, wear it all. Stallone even mastered casual layering equations in a time where men couldn’t have been more confused about how to dress themselves outside of the standard penguin suit. Stallone’s unapologetic bravado and calm-and-cool exterior made the perfection combination for him to become a style icon of the ‘70s and ‘80s.
Today, every male celebrity has a stylist to shape their style and provide direction for their red carpet ensembles, but not Stallone. The Rocky actor’s display of authenticity was inspiring and admirable. So maybe you didn’t share his same taste for out-there fashions of the time, but you still had to respect the man. Even one of the most influential fashion designers of the time, Gianni Versace, took notice and booked Stallone to star in a campaign opposite supermodel Claudia Schiffer in ’95.
Looking back at Stallone’s style evolution throughout the years, it’s easy to see how The Italian Stallion’s style flexes could have inspired today’s menswear style stars. Even for the average Joe, there’s plenty to take away from Stallone’s style moves. To highlight Sly’s impressive red carpet looks, here are 40 images of Sylvester Stallone’s style evolution from the ‘70s to today. Take notes, guys.
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The thick creme turtleneck, the unexpected leather trench—what’s not to love?
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Sly made silky bomber jackets look cool before Gosling made it big in Drive. The modern look of the bomber paired with a cool graphic tee and western belt still feels fresh for today.
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Print mixing isn’t easy, but Stallone wins this match.
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Before BDE, there was BSE: Big Stallone Energy. Every guy could use this no-pants-don’t-care attitude when grabbing their morning paper before taking on the day like a champ.
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Sly dresses up a pair of jeans like no other.
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A three-piece suit, folks. The action star cleans up nicely with precise tailoring.
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The wear-and-tear on Stallone’s hat adds some cool factor to his unique style. Many will try, but few can pull off a hat like this.
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Show us someone who can pull off a gigantic fur coat like this, we’ll wait.
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Stallone might have been in character promoting his ’81 film Victory, but there’s nothing costumey about this stylish long-sleeve polo shirt that’s a major menswear trend today.
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Chris Evans’ might look good in a cable-knit sweater, but The Italian Stallion does it best.
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One of Stallone’s most iconic fits that cemented his style-icon status. Do try this one at home, kids.
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The Rambo actor takes on the varsity look with a one-two punch of style.
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Now, this is how you dress like a total boss.
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Somehow the man can go out to eat at one of LA’s trendiest restaurants in two layers of jackets and still look damn cool.
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Never afraid to show some skin, Stallone knows showing off some muscle—even in a formal suit—is never a bad thing.
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Are you man enough to rock the banana hammock? Stallone shows some serious confidence while showing off his ripped muscles. Hey, if you worked hard on your sculpted physique, why not show it off?
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The not-so-mellow yellow color of this jacket is the perfect pop of color for cool style.
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Accessorizing your suit with an elegant brooch might be a standard style move for the A-List today, but Stallone stood out in ’86 rocking some lapel jewelry before it was cool.
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Rugby shirts made a comeback a few years ago and by looking at this outfit, it’s easy to see why.
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Pinstripes have never looked cooler—try to change our minds.
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It’s about the smallest details, like the subtle graphics on his tee and a braided-detail of his leather belt, that make this all-white look a total knockout.
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Yes, Stallone can even make a standard black tuxedo look badass.
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What can we say, the man has a great eye for suiting fabric. This look is seriously money.
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Style stars like Rami Malek know the power of a printed silky shirt today, but it’s possible he could have taken this style cue from Stallone in ’87.
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This one is all about the giant shield sunnies and innovative sneakers. We’ll forgive the super-tight T-shirt.
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Opt for a printed blazer to beef up an all-black outfit.
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Even when Stallone wore suiting, small embroidered details made him standout in any crowd.
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A classic moto and perfectly fitting jeans get a punch of style power with a bright colored tee.
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Can you guess the year on this one? It’s another unique detail that we come to expect from Stallone’s wardrobe.
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Seriously, even Stallone’s casual wardrobe essentials had interesting design details, like this mixed materials trench coat.
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Pro tip: Add some flair to your suiting with a silky shirt. This trend is back in style.
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This quintessential New York layering look is perfection.
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Guys like Dwayne “The Rock” Johnson and Ryan Reynolds love sporting a knit shirt with suiting, but Stallone wore this cool styling combo first.
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The western belt! The aviators! The mock-neck sweater! This is hands-down one of his best flexes.
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Okay, we spoke to soon—THIS is one of Stallone’s top style flexes. He wins just for rocking this Versace belt alone, but the overall effect is just too damn cool for words.
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In New York or Los Angeles, we could easily see this look being donned by the coolest tastemakers in town.
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Luxury fashion labels like Saint Laurent have been showcasing western skinny belts and cool, relaxed printed shirts for the past few seasons. Stallone was simply ahead of his time.
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Is it us or could you just see Momoa sporting this look next awards season, too?
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Everyday style made effortlessly cool with a utilitarian shirt, timeless sunglasses, blue jeans, and white sneakers.
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After ‘90s minimalism became the dominating style trend of the times, Stallone stored away his wild accessories and pops of color for good. Sure, his dad style isn’t as exciting as his ‘70s and ‘80s looks, but Stallone still knows the importance of showcasing your gains and keeping your look tailored.
