
While it’s fascinating to imagine what life was like way back when it was even cooler when you could see an actual photograph, it makes it almost palpable. We’ve assembled a collection of vintage photographs of people who had that special something—that unique coolness that so many of us strive for. Some photos are of famous figures from the past, while others are of everyday people just like us, who mark a moment in history. Let’s dive into the past.
#1: Mother’s Day Race, 1991
The public loved Princess Diana, and this photo is a perfect example of why. Among other things, she was known for breaking royal protocol and being down-to-earth and relatable, which the British royal family had not seen until then. This photo captures Diana showing her competitive side.

This action shot of Lady Di participating in a Mother’s Day race at her son William’s school is unprecedented. No one had ever seen a royal running barefoot in a skirt before! She was a truly elegant woman, even when she broke protocol and played soccer, and this photo of her showing her playful side makes her all the more relatable.