Guessing Your Family Photos: Clothing Edition!
23 Subscriber submitted photos
Hey vintage lovers!
Today's post is a little different and so much fun! I asked you all to submit your family photos, and I’m going to try to guess the exact year based purely on the clothing, hairstyles, and accessories… No pressure, right?
I’m seriously blown away by the number of submissions I received—thank you! For those of you who didn’t make it into today’s post, don’t worry. I put together a full-length YouTube video where I dive into 23 different submissions, so be sure to check it out at the end!
Okay, let’s dive into today’s picks. Time to put my vintage guessing skills to the test!
Photo 1: Kathy’s Family Snapshot
Now, this one might be a little blurry, but that doesn’t stop me from immediately falling in love with the girl on the far right’s dress! At first, I thought she was wearing a bolero jacket, but on closer inspection, it might actually be part of the dress. How incredible is that detail?
The entire vibe of this photo just screams mid-50s to me. The modest necklines, puffed sleeves, and those perfectly coiffed hairstyles—it all feels very classic. My guess? A family wedding. Everyone is dressed so beautifully, like they’re ready for a big celebration!
My Guess: 1953
Actual Year: 1956
Okay, so I was a few years off, but I’ll count that as a win! It’s clear we’re deep in the 50s here.
Photo 2: Cori’s Family Gathering
This one was actually submitted by my great aunt (shoutout to Grandma’s sister!)—and she sent a few, so let’s dive into the first one. This is
and her sister Launie, and wow, this one just has 90s written all over it. The floral shirt, the oversized T-shirts, that laid-back vibe… I’d say we’re smack in the middle of the 90s.My Guess: 1995
Actual Year: 1997
Cori also shared this photo with the caveat that she didn’t know the exact year, but she gave me some hints/family history.
Katherine "Katerina" Bartyzal was born in 1866 in Nová Hlína, Bohemia. She immigrated to the U.S. with her parents and siblings in 1891. Over her life, she married four times, had ten children, and at least 35 grandchildren, one of them was my great grandpa.
This one is hard for me! Based on the woman's wide-brimmed, decorated hat and high-collared blouse, both common in the late Victorian to early Edwardian era, I’d guess 1890-1910?
My Guess: 1903
Actual Year: Unknown!
Photo 3: Ricky’s Family Adventure
Okay, this one took me right back to my childhood. The baggy sweatshirts, those iconic 90s glasses, the white sneakers, light wash dad jeans—it’s such a time capsule. And can we talk about the whole family outing vibe? This is the ultimate 90s cool family!
My Guess: 1994
Actual Year: 1990s
At first, I was tempted to say 80s because of that fun patterned skirt/dress, but ultimately, I’m sticking with the 90s for this one due to that plain baggy t-shirt and gorgeous bangs. The 90s was all about simplicity + beautiful hair!
My Guess: 1994
Actual Year: 1990s
Photo 4: Anna’s Glamorous mom
Cue that TikTok sound—“let’s hear a little commotion for the dress!” I mean, could this be any more 1980s? The iridescent fabric, the lace details, that perfect perm, and the oversized bow on the waist! The pearl necklace and earrings are the cherry on top. I love this look—it’s so glamorous.
My Guess: 1984
Actual Year: 1987
Awwww! This is Anna’s mom and dad’s engagement photo. The dress is almost giving me The Notebook vibes with its nod to that 1980s/90s-does-40s/50s style. The white shoes and high-waisted pants definitely give off a 90s feel, but it can't be too far from the last photo since Anna's mom still looks so young… (Is it cheating to use the last photo?)
My Guess: 1992
Actual Year: 1993
Photo 5: Julie’s Family Photo
Unfortunately, this photo didn’t make it into the video since it was an email I received a long time ago, but this is Julie’s dad who was a “change of life baby.” I immediately recognized how similar it looked to my own great great great Aunt’s wedding photo taken in 1917, thus my guess is the same!
My Guess: 1917
Actual Year: 1917
I had so much fun doing this—it felt like a little time travel through your family memories, and I loved getting to see how styles and trends reflect the eras we all grew up in. Everything I know about vintage clothing came from my grandma’s collection, and this was such a great way to test my knowledge and learn about families and cultures different from my own.
If you’re as obsessed with family photo history as I am, you have to check out my full YouTube video where I guess 23 different submissions! It’s linked here, so go take a peek and let me know if I got your family’s era right.
Also- stay tuned for next week’s video where I chat with a historian from California about an incredible 1940s dress and the story behind it. I can’t wait to share it with you!
Hahah I love this so much truly a skill 🩷🩷🩷
This was 😊 fun