Some looks never go out of style. The classic sweater and shirt combo is one such choice. This fashion choice transcends trends and remains effortlessly stylish across generations.
One of these combinations is the classic sweater over a collared shirt, a look that has graced the big screen and been worn by television icons for decades.
From old Hollywood charm to modern heroes, let’s explore how some of the most stylish men in history have rocked this timeless look.
Classic Hollywood: The Sweater and Shirt Look
Marlon Brando in A Streetcar Named Desire (1948)
Before he became a Hollywood rebel, Marlon Brando had a classic and elegant style.
In A Streetcar Named Desire, he wore a black sweater layered over a crisp white collared shirt, proving Coco Chanel’s famous quote: “Simplicity is the keynote of all true elegance.”
Frank Sinatra in Ocean’s 11 (1960)
Frank Sinatra knew how to make a statement on stage and screen.
A great example is the original Ocean’s 11, where Sinatra made waves with his orange sweater and white shirt combination—a bold yet surprisingly polished choice that perfectly captured his confident, Rat Pack-era swagger.
Inspired by Sinatra's bold style? Explore our collection of 2-in-1 sweaters.
Sean Connery as James Bond in Goldfinger (1964)
The ultimate secret agent was known for his sharp tuxedos, but Connery’s Bond also mastered the art of looking polished yet relaxed.
In Goldfinger, Sean Connery sported a fine-knit sweater over a collared shirt, showcasing a more laid-back yet refined side of 007.
The Sweater and Shirt Combo: Mid-Century to Modern Style
Robert Redford in Three Days of the Condor (1975)
Offering a masterclass in style, Robert Redford’s rich sapphire sweater over a light blue shirt in Three Days of the Condor embodies the simple elegance of 1970s menswear.
Whether on the run or reading a book, Redford made sure to look sharp.
Pierce Brosnan as James Bond in GoldenEye (1995)
Fast forward two decades, and another James Bond embraced the same look as Sean Connery.
In GoldenEye, Pierce Brosnan wore a sapphire sweater over a collared shirt, reinforcing that even spies fighting post-Soviet Union villains appreciate the versatility of this look.
Jon Hamm as Don Draper in Mad Men (2007–2015)
Modern Takes on a Classic Look
Benedict Cumberbatch in Sherlock (2010–2017)
Few characters made intellect look as effortlessly stylish as Benedict Cumberbatch’s Sherlock Holmes.
Whether solving crimes or making a dramatic entrance, he often layered subtly textured oatmeal or brown sweaters over collared shirts, a look as refined as his deductions.
Elementary, yet undeniably sophisticated.
Steve Carell in Crazy, Stupid, Love (2011)
One of the most iconic style transformations in film, Crazy, Stupid, Love saw Steve Carell’s character go from "The Gap" to GQ-worthy.
After taking fashion advice, he stepped out in a perfectly fitted sweater-over-shirt combo, proving that dressing well is a skill anyone can master.
Josh Radnor as Ted Mosby in How I Met Your Mother (2005-2014)
Daniel Craig as James Bond (2006-2021)
Rounding out our list is the most recent 007, Daniel Craig.
While Bond's choice of watches and cars might have changed (from Rolex to Omega, from Aston Martin to BMW), the common denominator over the decades has been his sweater-and-shirt combination—proving that some looks never go out of style.
Why the Sweater-and-Shirt Combo Endures
What makes this combination so enduring?
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Versatility: It works in casual, business, and even semi-formal settings.
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Timeless: Decade after decade, icons have chosen this look.
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Effortless: It’s stylish without trying too hard.
At Flying Point Apparel, we’ve refined this timeless look with modern craftsmanship.
Our 2-in-1 sweaters give you the perfect layered style without the bulk—because looking sharp should always be this easy.
Get the iconic look without the hassle. Shop our collection of 2-in-1 sweaters and experience the effortless style and comfort for yourself.