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Vintage Photos Where Not Everything Looks As it Should

Old photos get weirder with time.

By Micaela Montaña

Published 4 weeks ago in Funny

Ahhh, the good old days, back when men wore hats, women wore gloves, and absolutely no one thought to question why Uncle Frank was wearing that costume. These snapshots are the sepia-toned mysteries our ancestors forgot to explain, leaving us with only one conclusion: weirdness ages like fine wine.


There’s something deliciously off about these old photos, they have background details that whisper: “Something’s not right here…” It’s nostalgia with a side of “Wait, what am I looking at?”


So step into the time machine, but keep one eyebrow raised. Because behind every black-and-white grin lurks a story stranger than fiction and sometimes, history’s most charming moments are also its most unexplainable.

  • 1

    The Laughing Policeman

    A publicity photo for The Laughing Policeman, a popular song in 1920s England.

    The Laughing Policeman

  • 2

    Halloween, 1950s-Style

    Here is an uncle in the 1950s dressed as a baby, drinking from his "bottle."

    Halloween, 1950s-Style

  • 3

    Seeing Double

    Matching outfits in 1952.

    Seeing Double

  • 4

    Big Hair, Don’t Care

    Hairstyle in Tampa, Florida, 1985.

    Big Hair, Don’t Care

  • 5

    The Great Snail Chariot Race of 1954

    Martin Witter and two snails (from his larger snail team) in chariot race, 1954.

    The Great Snail Chariot Race of 1954

  • 6

    When Cats Had Their Own Pool Parties

    Cat Swimming Pool at Fontainebleau Hotel, Miami, 1955.

    When Cats Had Their Own Pool Parties

  • 7

    1950s Circus Act

    A circus act in the 1950s where a father throws knives near his baby.

    1950s Circus Act

  • 8

    Only in 1953

    Win a casket! 1953.

    Only in 1953

  • 9

    1935 Had Questions

    An unusual horse costume, 1935.

    1935 Had Questions

  • 10

    Street Swimming, NYC-Style

    The kid is swimming in the gutter, 101st St and Manhattan Ave, NYC, 1949.

    Street Swimming, NYC-Style

  • 11

    Basement Picnic at Grandma’s

    Picnic at Grandma's in the basement. Why do we need an umbrella? 1960.

    Basement Picnic at Grandma’s

  • 12

    Toilet Paper Terror

    Louis was mortified to see he had some toilet paper on his shoe, 1959.

    Toilet Paper Terror

  • 13

    Stuffing Trees with Sorority Girls

    A competition involving stuffing trees with University of Maine sorority girls, 1961.

    Stuffing Trees with Sorority Girls

  • 14

    1946’s Mysterious Sky Glow

    UFO? Meteor? 1946.

    1946’s Mysterious Sky Glow

  • 15

    The Sphinx Gas Pump

    Sphinx gas pump in London, England, circa 1930.

    The Sphinx Gas Pump

  • 16

    Zombie Bride Chic

    1964 bride with full white face, looks like a zombie.

    Zombie Bride Chic

  • 17

    Octo-Boy

    Octo-Boy with his Squid Trunks, 1945.

    Octo-Boy

  • 18

    Don’t Touch the Hat

    Nobody dares remove Mr. Peanut's hat, now he's glowering. Staten Island Ferry, NYC, 1972.

    Don’t Touch the Hat

  • 19

    Dinner with Gators

    Dinner with the gators at Luna Park Alligator Farm, Lincoln Heights, Los Angeles, CA, circa 1930s.

    Dinner with Gators

  • 20

    Meet the Portable Donkey

    Portable household donkey with his owner Ron Brewer, Southall, England, 1965.

    Meet the Portable Donkey

Categories:

Funny Retro

Tags:

vintage photos old photos weird weird photos funny funny photos weird vintage photos
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