50 Photos From The Past That Can Only Be Labeled As “Cool”

Cool Old School and Cool Past Pics have both been around the block for a while. They’re not as old as the photos they share, of course, but they both launched on Twitter in 2013. Since then, each page has amassed about 100k followers and shared over 1,000 tweets. From featuring photos of celebrities in their youth to snapshots of cultural events that rocked the world, these accounts are always entertaining.

From perusing the pictures on this list, you might learn more about your favorite film, what it would have been like to be in high school at the same time as your parents, or what you would have worn if you lived in New York City 50 years ago. Although times change rapidly, these photos are great reminders that people are just, well, people. We go to the same places today, and we enjoy the same activities, like attending music festivals and grabbing a meal with our friends. So enjoy the nostalgia of these pics, and put on some tunes from your favorite decade to really set the mood. 

To gain some insight from an expert on vintage pics, we reached out to Maureen Taylor, the Photo Detective. Maureen specializes in helping clients understand their family history and themselves through investigating old photos they bring her. “I start by studying clues within a picture — a hairstyle, a sign in the background, or the shape of a shirtsleeve — in order to identify a person, place or era,” Maureen writes on her website. 

“What follows from my genealogical expertise is uncovering the story behind the images of the past.That could mean shedding light on how those pictures fit into your family tale. Or discovering the history of the area in which those people lived — even if that’s locally in my small state of Rhode Island or around the world in Australia.”

First, we wanted to know what inspired Maureen to become a photo detective and expert on vintage photographs. “I worked for a historical society and while folks came in to look at books about their family history, hardly anyone asked if there were photos,” Maureen told Bored Panda. “It surprised me. It’s true that every photo tells a story.”

“Some are amazing tales like the ones on Cool Old School, and some represent more mundane moments (for instance, the sitter bought a new hat),” she explained. “All photos capture a moment in time—what were the people thinking, why did they have a picture taken, and how do those images fit into the historical context of the times. The details add up to fill us in and the lives of the individuals help fill out the story.”

We also asked Maureen why it’s important for us to hold onto old photos and keep viewing pictures from the past. “So much of history isn’t written down,” she told Bored Panda. “I see it in client photos. For instance, obsolete technology and businesses that barely left a mark. But the people and places in those images existed. They lived everyday just like we do. The photos might represent an important moment in their lives such as a wedding, or a baby that didn’t live to beyond infancy.”

“To truly understand the past, we have to talk with people about their lives and study the historical record, BUT also look at the photos and movies, because local, national, international and family history is in the tiniest details depicted,” Maureen says. “Each photo is a mystery to be solved.”

We also asked Maureen what we can learn from these vintage photographs. “Photos show us how we lived and loved,” she said. “They depict past generations by illustrating what was important to a person from fashion to friends. I believe each image is a time portal, a freeze frame of the past, a moment worth savoring. It captures a second that won’t happen again. Looking at pictures triggers memories, not just about the time captured by the shutter. There are related memories as well.” 

“When I showed my mother a picture of her with her siblings when she was five, I was seeking answers to why and where they posed,” Maureen explained. “Instead, she shared a story about the first day of school and how her eldest sister bought her new clothes. Think about what you feel when you look at an image. They often leave us with a sense of nostalgia and longing for what came before. It’s our connection to the days we lived or those lived by our ancestors. Save them or lose a piece of the past that might not be recoverable.”

Finally, Maureen added that she “never met a photo that [she] didn’t want to know more about”. If you’re interested in consulting Maureen about a photo of your own or you’d like to hear more about her process, be sure to check out her website right here. She even has a podcast covering topics from genealogy to fashion history on Twitter, so if you’re interested in that as well, you can find it right here. 

We also reached out to photographer, vintage enthusiast and the man behind Vintage and Vogue Photography, Mark Bilash, to hear his thoughts on the topic. But first, we wanted to hear what inspired Mark to pursue a career in photography. "As a young boy I was fascinated with how you could 'freeze a moment in time' with a photograph," he told Bored Panda. "From there I began to love the creative aspect of lighting, to set a mood or tone in photography. I can’t play an instrument, sing, or paint – so this was my creative outlet."

We also asked Mark about his personal style of photography. "I love the style, fashion and appearance from the 1920s to the 1960s," he shared. "This led me to specialize in creating images that have that same look and feel from these decades. Classic Hollywood, Pinup, and Film Noir are some of my favorites genres from these decades. If I’m shooting a modern session, I do like to add a 'vintage flair' to it with possible props or an editing style."

When it comes to what Mark loves most about vintage photos, he told Bored Panda, "Seeing a true vintage photo just draws me into a time and place that is so different from now. The buildings, the fashion, the cars, and the hairstyles are all 'eye candy' for me."

"For example: A basic photo of a parking lot full of cars from 1950, is like a work of art," Mark shared. "Every vehicle has such stunning style as opposed to nowadays. Plus it is always a bit of a history lesson. Seeing what once was and how things have changed over time. The craftsmanship of yesteryears compared to the cost-cutting of today. That is why I love creating Vintage Styled images. Having people dress in an era of spectacular fashion and stunning hairstyles is always such a rush. Also makes people appreciate the past."

We also asked Mark why holding onto pictures from the past is important. "Photos not only record a specific moment in time, but many also capture an emotion from that moment," he explained. "Since we can’t time travel yet, this is the best way possible to do so. Looking at an old photo is like peering through a window into the past. It’s also an important record of our history, whether it’s a personal history or more of a general history."

"People do not live forever, but their memories and lives can be preserved through photographs. Instead of just reading about someone or something from the past, a photo gives us a real life personal view of days gone by."

"My ideal 'dream vacation', would not be to travel to an exotic location. Instead – if it were possible – I would like to travel back in time and visit my locale during the 1920’s – 1950’s," Mark shared with Bored Panda. "Just walking around the neighborhood and seeing my city as it once was. All the interesting streets, shops, and people that are around. Take in the whole experience. That would be amazing!"

If you'd like to check out Mark's wonderful, vintage themed photos, you can visit his website right here.

We hope you're enjoying this list of cool old school pics and pics from the past that might give you a bit of nostalgia, or anemoia, nostalgia for a time you never experienced. Be sure to keep upvoting the photos that you wish you could have been around for, and then let us know in the comments which ones you'd time travel to if you had the opportunity. Then, if you're interested in checking out even more photographs from days past, I recommend you head over to this Bored Panda article next.