17 Awkward and Hilarious Family Photos

Written by Alina Wang on May 13, 2025

A family portrait from the 1980s shows three children sitting in front of a man, with a woman standing behind them. The group is indoors, surrounded by vintage decor and patterned wallpaper.

u/brandangb via Reddit.com

When it comes to family portraits, the best photos are the ones that lean all the way into the cringe. From bowl cuts and braces to matching neon sweaters and awkwardly-forced smiles, these retro family portraits are a time capsule of questionable fashion choices — and even more questionable hairstyles. Whether it was dad’s creepy-looking mustache, mom’s gravity-defying perm, or the kids’ unimpressed, empty stares, here are over a dozen hilarious family photos from the ’70s, ’80s, and beyond.

1. The Year Was 1992, and Mullets Were Everywhere …

A family of four poses for a portrait wearing matching red clothing. The parents stand behind, the father with a mustache and mullet, the mother with voluminous blonde hair. Two young children smile in front. — u/krazyk850 via Reddit.com

u/krazyk850 via Reddit.com

2. When Your (Vampire) Photoshoot Also Doubles as a Height Chart

A vintage black-and-white photo of a family with two adults and four children, all standing in a row by height, from shortest to tallest, wearing early 20th-century clothing and facing the camera. — u/Tyagi_rishu via Reddit.com

u/Tyagi_rishu via Reddit.com

3. It’s Giving Sass With a Side of Blue Steel

Five people stand in a line outdoors in front of snowy pine trees, all wearing matching red shirts with graphics and blue jeans, with their hands in their pockets, looking toward the camera. — u/Unique-Acadia-5429 via Reddit.com

u/Unique-Acadia-5429 via Reddit.com

4. ‘Creepiest Version of the Clauses Ever.’ You. Don’t. Say.

u/Consistent_Artist_67 via Reddit.com

u/Consistent_Artist_67 via Reddit.com

5. Not Sure What’s Happening Here, But the Doll? Absolutely Not.

A vintage black-and-white photo of eleven people wearing white, hooded outfits with scarves or wraps around their heads, posing in two rows—some standing, some sitting—against a dark backdrop. — u/Market_Massive via Reddit.com

u/Market_Massive via Reddit.com

6. When Denim Is Life

A family of four poses for a studio portrait, all wearing blue denim shirts. The adult man's face appears digitally edited onto each family member, including the woman, older girl, and baby. The background is blue. — u/Sarahhatessunglasses via Reddit.com

u/Sarahhatessunglasses via Reddit.com

7. Bowl Cut Swagger, Circa 1985

Two young children pose for a holiday photo in front of festive decorations. The older child with a blond bowl cut wears a red sweater, while the younger child, also blond, smiles and wears a red outfit with a patterned collar. — u/transphotobabe via Reddit.com

u/transphotobabe via Reddit.com

8. Photographic Proof That Moms Are ALWAYS Watching (and Judging)

A young man in a tuxedo and top hat smiles while seated, with an older man in a suit and a woman in a floral dress standing behind him, posing for a formal portrait against a dark studio backdrop. — u/joelsopp via Reddit.com

u/joelsopp via Reddit.com

9. When the Resemblance Is Unmistakable

A family of four poses together in a studio. Two adults sit in front; the woman wears a red cardigan, and the man a maroon sweater. Two teenagers stand behind them, both smiling and wearing sweaters. — u/pike1990 via Reddit.com

u/pike1990 via Reddit.com

10. Who Doesn’t Love a Good ‘Glamour’ Shot From the ’80s?

A woman with short dark hair smiles, wearing a sparkling blue off-shoulder dress, a matching necklace, earrings, and a ring. She holds her hand to her cheek, posing in front of a soft blue textured backdrop. — u/deleted via Reddit.com

u/deleted via Reddit.com

11. This One’s Heavy on the ‘Succession’ Vibes

Eleven people in formal attire pose seriously around a piano and a sofa in a well-decorated living room, some holding drinks or cups, with vintage-style decor and sunlight streaming through the windows. — u/ykkz via Reddit.com

u/ykkz via Reddit.com

12. Guess Dad Didn’t Have Time To Change Into His Matching Jammies

Four women in matching pajamas and one shirtless man pose in front of a decorated Christmas tree. The women are sitting and kneeling, while the man is standing behind them, all smiling for the holiday photo. — u/Familiar_Big3322 via Reddit.com

u/Familiar_Big3322 via Reddit.com

13. Turtlenecks: Stylish, Yes. Bite-Proof? Not So Much

Three young people in white turtlenecks sit closely together, each laughing while holding two dogs that are baring their teeth at each other with mouths open, creating a chaotic and humorous scene. — u/Familiar_Big3322 via Reddit.com

u/Familiar_Big3322 via Reddit.com

14. When the Pup Also Doubles as Your Twin, Circa 1982

A man with a mustache and a woman with long blond hair, both wearing purple shirts, pose outdoors for a portrait. The man holds a small brown dog. Trees and part of a house are visible in the background. — u/shepersisted2016 via Reddit.com

u/shepersisted2016 via Reddit.com

15. No JCPenney Shoot Is Complete Without This Pose…

A man and woman sit on the floor facing each other, legs intertwined, smiling at the camera. They both wear glasses and casual clothes, sitting against a plain gray wall and wooden floor. — u/missalleycat01 via Reddit.com

u/missalleycat01 via Reddit.com

16. … Or This One

A group of nine adults, all wearing black turtlenecks, pose in three rows, each resting their chins on the hands of those below. The background is light and softly blurred, creating a playful, staged family photo effect. — u/to_the_hunt via Reddit.com

u/to_the_hunt via Reddit.com

17. This Seems Accurate

A smiling couple poses together in front of a metal fence, while two children in the background playfully fight or wrestle with each other. Trees and an overcast sky are visible behind them. — u/[deleted] via Reddit.com

u/[deleted] via Reddit.com

Need more good laughs?

Check out 12 Stupidly Expensive Versions of Everyday Products to roll your eyes at life’s absurd luxuries. You should also check out 20 Absurd Things Rich People Do Just Because They Can and 15 Hobbies That Prove the Wealthy Live on Another Planet.