20 Vintage Photos of Ernest Hemingway That Are Pure Old-School Cool

Celebrity History April 8, 2025

Ernest Hemingway is one of those famed authors that to so many represents an unrivaled level of old-school cool. Whether you’ve gotten lost in one of his books like “A Farewell to Arms” or “The Sun Also Rises”, you’ve very likely heard one person or another ramble on about how much they love his succinct, powerful prose. We’ll take a look at a collection of vintage photos that captures some of Hemingway’s unmistakable old-school cool.

1. Ernest Hemingway and his son Gregory, Sun Valley, Idaho

A man in a cap and vest sits on a wooden dock by a river, with his arm around a boy lying down next to him. Two rifles rest on the dock beside them. The landscape features clouds, hills, and water in the background.
crowe410

So many times Ernest was caught deep in thought.

2. Ernest Hemingway and his hunting dog (1940s)

A man crouches in a field with tall grass, holding a rifle. He wears a coat and glasses, focusing intently. A black dog stands nearby. The background features distant hills under a cloudy sky. It's a black and white image.
zacht180

You can just tell that Ernest Hemingway’s hunting dogs were all business out there.

3. Writers Janet Flanner and Ernest Hemingway in the cafe Les Deux Magots, Paris, France, 1945

Two people in military attire sit at a table, one holding a document and both looking at it intently. There are drinks and glasses on the table. A poster and a light fixture are visible in the background.
ibkeeper

These look like especially serious times.

4. Ernest Hemingway, Sun Valley, Idaho, 1940

A man sitting on a wooden chair, writing on a pad of paper with a pen. He is wearing a heavy coat and his left leg is resting on another chair. A large window or door is open, showing an outdoor patio area.
robertcappa

Oh to have peered over his shoulder and gotten a look at whatever it is that he was writing.

5. Ernest Hemingway with model Jean Patchett, 1950s

A woman and a shirtless man sit on a sofa in a living room, each petting a cat. The man holds a drink. A rocking chair and mounted animal head are visible in the background. The scene is relaxed and casual.
marinekingprime

Ernest looking nothing if not at ease.

6. American Author Ernest Hemingway aboard his Yacht, circa 1950

An elderly man with a white beard and hair sits inside a cozy, wooden boat cabin. He wears a striped shirt and a brown vest. Fishing rods are mounted above, and a radio is visible in the background. The atmosphere is warm and rustic.
marquisofchaos

Ernest Hemingway certainly loved his boats.

7. Ernest Hemingway on safari in Kenya with his 4th wife Mary in 1953

A man and woman stand outside near thatched-roof huts. The man wears a wide-brimmed hat and boots, while the woman is in casual attire. The scene is under a clear blue sky with a rural backdrop.
matewan1998

If there’s one thing we know about Ernest Hemingway it’s that he certainly loved his time on safaris.

8. Authors Ernest Hemingway (L) & Sinclair Lewis, 1940s

Two men shaking hands outdoors, near a ship. The man on the left is wearing a light shirt and appears casual. The man on the right is in a suit and hat. Both are smiling, standing by parked cars with the ship in the background.
rockystl

Just a couple brilliant minds colliding for a historical moment.

9. Ernest Hemingway skiing in Gstaad, Switzerland, February, 1927

Smiling person standing on skis in a snowy landscape, with dense, snow-covered evergreen trees in the background. They wear a sweater, dark pants, and ski goggles, holding ski poles.
str33twise3

Ernest Hemingway could probably really put on a show out there on the slopes.

10. Ernest Hemingway in an ambulance of the Red Cross in Italy, circa 1910s

A man in a military uniform sits in the driver's seat of an old vehicle, looking at the camera. The vehicle appears to be part of a vintage military transport unit. The background shows part of the vehicle’s structure with a number "4" visible.
ladrada

It’s always wild to think about all of the times that Ernest must’ve had during the war.

11. Ernest Hemingway with pigeons, Piazza San Marco, Venice, Italy, 1954

A man in a suit jacket stands outside a historic building, holding and surrounded by pigeons. The building features ornate architecture with arched windows and spires. Another person is visible in the background.
anonymous

It’s quite funny to reflect on just how many genius minds had an unwavering love for the pigeons in this world.

12. Ernest Hemingway and his three sons with Blue Marlin on the Bimini docks, 193

A man and three children stand on a dock beneath four large, hanging fish. The children wear swimsuits, and the man is in a short-sleeved shirt and pants. Other people and a boat are in the background.
twissurface

Ernest had a knack for reeling in some larger-than-life catches.

13. Ernest Hemingway showing off his boxing form in the 1950s

A man with a beard, wearing boxing gloves and no shirt, is sparring playfully in front of a mirror. The reflection shows him in a boxing stance, suggesting a light-hearted practice session in a dimly lit room.
fredsr

Ernest certainly did love his time in the boxing ring.

14. Ernest Hemingway boxing in Africa, 1954

A bearded man wearing a beanie and boxing gloves playfully spars with another man in a white tank top outdoors on a grassy field. Two onlookers stand in the background, with trees and hills visible.
philyesplz

It never seemed like a bad time to Ernest to get a little boxing in.

15. Ernest fixing himself one of his favorite beverages

An older man with a beard is pouring a drink into a glass at a counter with several bottles. He is wearing a vest and shirt in a room with a mounted antelope head on the wall in the background.
deleted

He was certainly known to do such a thing, and quite often at that.

16. Ernest Hemingway and his son Gregory, 1941

A man in a cap and vest sits on a log beside a young boy wearing a blue sweater. They're outdoors on a sunny day with hills in the background. Both are smiling, creating a warm, friendly atmosphere.
aintachance

A beautiful moment caught between a father, above all else, and his son.

17. Ernest Hemingway Sitting on a Deck Chair at his Home in Cuba (1947)

A man sits in a white chair on a patio, surrounded by lush greenery. He's wearing a light shirt, shorts, and a brown jacket, with his legs crossed and holding a book. The background features plants and trees under a bright sky.
itkindalike

Ernest loved to get out to Cuba to get on with wrestling that blank page just a bit more.

18. Ernest Hemingway and one of his polydactyl cats, 1954

A bearded man is seated on outdoor steps, holding a black and white cat. He wears a brown shirt, beige pants, and boots. Behind him, a door and large plants are visible.
desevlo

I wonder if Ernest Hemingway and Charles Bukowski could’ve found a bond over their shared love for cats.

19. Noel Coward chatting with Ernest Hemingway at Sloppy Joe’s Bar in Havana

A group of people sit and converse in a bustling indoor cafe. In the foreground, two men are engaged in conversation at a table, with a lively crowd in the background. The setting has a vintage ambiance.
mydoggoldi

Man, it would’ve been fun to have been around this part of Havana that day.

20. Correspondent in the Spanish Civil War, Ernest Hemingway, 1937

A historical black-and-white photo showing a group of soldiers engaged in conversation with a civilian man in a suit. The soldiers wear military uniforms and carry rifles with bayonets. One soldier gestures with his hand while talking. Trees are in the background.
burntvalleys

Nice touch with the glasses there, Mr. Hemingway.

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