23 Vintage Photos of JFK’s Presidency

Written by Rachel Schneider on June 12, 2025

Two black-and-white photos: On the left, a smiling man in a suit waves from a convertible as a woman in a hat sits beside him, and a crowd looks on. On the right, the man stands speaking on a chair to a group of children.

John F. Kennedy’s presidency may have lasted just over a thousand days, but the images from that era still feel larger than life. They show us a president full of energy and charm: playing with his children under the Resolute Desk, kissing his father’s forehead, shaking hands with future leaders. They also reveal the whirlwind of history unfolding in real time: tense campaign stops, international diplomacy, and, ultimately, a nation in mourning. These photos captured during JFK’s leadership depict a bygone era gone all too soon.

1. Moments Before the Assassination

A motorcade with an open-top black car carrying a man in a suit and a woman in a pink outfit passes through a crowd-lined street. Police escorts and onlookers are visible, some waving and taking photos. — Walt Cisco, Dallas Morning News / Wikipedia

2. Young John F. Kennedy Jr. Waiting for His Dad to Land

A young child in red suspenders stands on a path with hands behind their back, watching a helicopter flying low in the sky over a grassy field. Trees and a fence line the background under a clear sky. — sputnik-the-sages / Reddit.com

3. Nancy Pelosi Meeting President John F. Kennedy After His Inauguration

A young woman in a vintage, sleeveless dress and white gloves stands beside a man in a tuxedo and bow tie. Both are smiling in a formal indoor setting, with the man holding a folded paper. — eaglemaxie / Reddit.com

4. JFK Kissing His Dad’s Head After His Stroke

A man in a suit gently kisses the forehead of an older man with white hair, who is sitting in a wheelchair and wearing a light blue robe. The interaction appears caring and affectionate. — -VFL- / Reddit.com

5. Young Bill Clinton Shaking JFK’s Hand

A group of young men in white shirts and veterans in hats gather outdoors as a man in a suit shakes hands with a smiling young man. Trees fill the background. — LongSlayer

6. The President in His Office With John F. Kennedy Jr. Playing Under His Desk

A man works at a large wooden desk in an office, while a young child peeks out from a small compartment beneath the desk. — UserDeleted / Reddit.com

7. JFK Speaking in West Virginia During His Campaign in 1960

A man in a suit stands on a wooden chair, speaking to a crowd of people, including children, gathered outdoors in a small town with hills in the background. The audience listens attentively. — xbftw / Reddit.com

8. Visiting Ireland in 1963

A man in a suit walks beside a uniformed officer outdoors, with people and a crowd in the background. The photo appears to be from a past era, possibly the 1960s, and is in black and white. — Liamerzz / Reddit.com

9. JFK Going for a Ride With His Daughter Caroline in the Honey Fitz

A man wearing sunglasses and a dark sweater sits closely beside a young girl with blonde hair, both looking into the distance on a cloudy day, possibly during a boat ride. — UserDeleted / Reddit.com

10. Princess Grace of Monaco With JFK at the White House

A man in a suit gestures while speaking, and a woman wearing a decorative headpiece stands beside him, looking at him attentively. The image is in black and white. — StrawberryFew1311 / Reddit.com

11. The Royal Couple’s Visit to the White House

Four people stand at a building entrance; two women in formal dresses and two men in suits. One man gestures while speaking. A group of people stands behind them in the doorway. The setting appears formal and historic. — butterflypoo69 / Reddit.com

12. Tea Time With Caroline

A man in a suit sits in an armchair, sharing breakfast with a young girl in a light coat. The meal is on a tray table in a bright, elegant living room with large windows and upholstered furniture. — better_abort / Reddit.com

13. Quality Time With Junior

A man in a suit sits on the steps of a white-columned building, helping a young child in a red coat with their shoe. Trees and garden beds are visible in the background on a sunny day. — froggysaysno / Reddit.com

14. An Important Letter From a Disgruntled 7-Year-Old

A handwritten letter from a child to President Kennedy, requesting that television programs start after 8 PM so he can watch Dick Tracy and The Action Hour. The letter is signed by Bruce Burchardt, age 9. — morganmonroe81 / Reddit.com

15. Massive Crowd at a Campaign Stop in 1960

A black-and-white photo shows a large crowd filling a city street to see John F. Kennedy give a campaign speech from a stage atop a flatbed truck in front of the Hotel Altamont in Hazleton, Pennsylvania, in 1960. — Silverpicker97 / Reddit.com

16. JFK at a Ball Game With His Sister Jean Ann

A black and white photo of a smiling man in a suit and tie sitting next to a smiling woman with wavy hair, both appearing happy and engaged, possibly at a public event. — UserDeleted / Reddit.com

17. Lyndon B. Johnson Yelling at a Plane’s Pilots to Cut Their Engines so JFK Could Speak

A man in a suit and hat raises his arm and shouts in the foreground, while another man in a suit, with recognizable features, stands behind him, appearing concerned, among a crowd of people. — zadraaa / Reddit.com

18. JFK Talking to Former President Dwight Eisenhower After the Bay of Pigs Debacle

Two men in suits walk side by side on a stone path through a wooded area. One carries a hat behind his back. Both are seen from behind, surrounded by tall, leafless trees. — HelloSlowly / Reddit.com

19. JFK and Jackie Coming Home From the DNC in 1960

A man in a suit waves from the back of a convertible car while smiling. A woman in a hat and gloves sits beside him, also smiling. A crowd and police officers are gathered around, cheering and taking photos. — Conscious-Dingo4463 / Reddit.com

20. Talking to Coal Miners While Campaigning in West Virginia

A man in a suit sits on a step, surrounded by workers in hard hats and work clothes. The workers stand and sit around him, listening intently. The background is industrial and weathered. — Teresa_Blackshaw / Reddit.com

21. Campaigning Door to Door

Black-and-white photo of a boy standing at the bottom of wooden steps, talking to three girls on a porch of a rural house. The ground is bare, with a broom and scattered items nearby. The scene is outdoors. — DenMother8 / Reddit.com

22. JFK and His Daughter Caroline on Halloween: Who Wore it Better?

An adult man sitting in a green armchair smiles while posing with a child wearing a cartoonish mask and costume. Both are mimicking the same thoughtful pose, with one hand resting on their chin. — fleurjackie / Reddit.com

23. Woman Reading the Newspaper After JFK’s Assassination

A woman with styled hair reads a newspaper with the headline "President Killed" in front of a store window displaying a sign that says the store is closed in mourning for President John F. Kennedy's assassination. — Sleeeepy_Hollow / Reddit.com

Want more presidential content?

You might be interested in 22 Photos of Richard Nixon’s Presidency and Political Career and Turning Memoirs Into Millions: The Most Lucrative Presidential Book Deals Ever. For a look at how much it costs to run a presidential campaign — even an unsuccessful one — be sure to read The 10 Most Expensive Presidential Campaigns That Ended in Defeat.