These Vintage Photos Are All the Sweater Weather Inspiration You Need

WHEN HARRY MET SALLY... Meg Ryan Billy Crystal 1989  Columbiacourtesy Everett Collection
Photo: Columbia Pictures/Courtesy Everett Collection

At long last, it’s officially sweater weather. As the temperatures drop and we retire our summer staple cutoffs and tank tops in favor of cardigans and pullovers, we invite in this season’s hero: the knit

But while many of us surely dream of sitting by the fire wrapped in a cozy sweater as we sip from a mug of cocoa, we live in an era where our knits aren’t what they once were. When considering the insulating wool of Billy Crystal’s sweater from When Harry Met Sally versus the polyamide hellscape that comprise most of today’s outerwear, writer Ellory Smith wrote: “The quality of sweaters has declined so greatly in the last twenty years that I think it genuinely necessitates a national conversation.” 

Indeed, so much of the finest sweater weather inspiration comes from one source: vintage photos of older men, many of them famous. When it comes to dressing for the coziness and durability that autumn demands, these distinguished gentlemen have paved the way for people of all genders to try their hand at some truly impeccable fall fashion. 

Whether we’re feeling envy over Robert Redford’s sweaters, or would love to raid Alain Delon’s closet, Hollywood’s male mainstays are becoming unintentional womenswear icons. So if Burt Reynolds’s pullovers or Sean Connery’s cardigans aren’t on your fall mood board yet, perhaps consider looking to these well dressed men for fall fashion inspiration. 

Sean Connery during Norris Church Art Exhibition at Madison Galleries in Hollywood California United States 22nd March 1989.

James Bond himself, Sean Connery makes an excellent case for a patterned, single-button cardigan. Consider styling as Connery did, with a polo—with a popped collar. 

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Actor Morgan Freeman sits on a stoop and smiles for the camera in these four photos on a single contact sheet in Los...

In this contact sheet, Morgan Freeman shows off his personality and his stellar taste. From the patterned swearer to the corduroys, there’s no part of this look we wouldn’t wear.

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French actor Alain Delon on the drums 1959.

Alain Delon’s v-neck sweater leaves ample room for showing off necklaces.

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THE TONIGHT SHOW STARRING JOHNNY CARSON  Pictured  Actor Burt Reynolds host Johnny Carson on February 25 1987

Burt Reyolnds stopped by Johnny Carson’s show in a beautiful lilac crewneck.

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Portrait of Marlon Brando in A Streetcar Named Desire

Marlon Brando’s cropped sweater is great for defining a waistline and showing off the pants.

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CLARK GABLE  Pictured Actor Clark Gable

Clark Gable wears a preppy classic with this white sweater with black and red stripes.

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Singer Mick Jagger of The Rolling Stones during rehearsals for an episode of the Friday night TV poprock show 
Ready...

We can feel the coziness of Mick Jagger’s turtleneck from here. 

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American actor Paul Newman  circa 1955.

They don’t stitch like Paul Newman’s cardigan anymore. 

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WINDSOR UNITED KINGDOM  JUNE 01 Prince Charles Wearing A Bright Yellow Hermes Sweatshirt Saying 
 Happy Hermes
 At...

King Charles, then the Prince of Wales, rocked this graphic Hermès pullover.

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Robert Redford Leaning on a Brick Wall

Try draping a sweater over your shoulders like Robert Redford did over his button-down.

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Actor Robert Redford. Redford wears a sweater with the letter W on the front and a wide white collar. ca. 1960
s.

Sorry but we absolutely must include Redford twice thanks to this collegiate letter sweater over a collared shirt.

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UNITED KINGDOM  NOVEMBER 06 Samuel L Jackson The 51st State World Movie Premiere Held At The Curzon Cinema In Mayfair...

Samuel L. Jackson’s navy blue turtleneck is equally as fabulous as his kilt. 

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