“First Instagram Post”: 40 Rare Celebrity Photos Taken Many Years Ago

Fashion is a moving timeline, and celebrities have always been its trendsetters. As years go by, it’s fun, and sometimes shocking, to look back at what was once considered “cool.”

From butterfly clips to hip-hugging jeans, the early 2000s had a flavor of its own. But fast forward to today, and those same stars wouldn’t be caught dead in those outfits. It’s a reminder of how style evolves, sometimes fast, sometimes in full circles. 

To dig deeper into this transformation, we chatted with Kayal, a fashion stylist based in Mumbai. Kayal has worked with some of Bollywood’s biggest names and knows firsthand how quickly trends come and go.

“Fashion evolves with time,” she said. “It’s not just about clothes, it’s a reflection of the times, the attitudes, and sometimes the rebellion of a generation.” According to her, the 2000s were expressive but a little wild compared to today’s more curated styles.

One look that dominated early 2000s wardrobes? Capri pants. “Capris were everywhere,” Kayal laughed. “They were often paired with spaghetti tops, studded belts, or layered tank tops. Juicy Couture tracksuits were also a huge deal. Velour was in, and so were logos—lots of them.” Back then, more was more, and subtlety wasn’t really part of the fashion vocabulary. Celebs were bold, flashy, and very Y2K.

Still, not everything from that era vanished. Some pieces have aged gracefully and even stood the test of time. “Take a great leather jacket or a clean white shirt,” Kayal noted. “They were loved then, and they’re loved now. Some items just work across decades because they adapt so easily. A classic trench, for instance, can be styled ten different ways depending on the trend.” These staples prove that a few things truly are timeless.

Of course, not everything needs to make a comeback. “Low-rise jeans, for example, I’m happy to leave those in the past,” Kayal grinned. “And those tiny shoulder bags? Cute, but wildly impractical. We romanticize them now, but they weren’t always fun to use. We’ve learned from our mistakes, and that’s part of growing in fashion too.” In many ways, the cringe factor is what makes old trends memorable.

Over time, fashion has become more experimental and inclusive. Kayal explained that today’s celebrities are far more daring and individualistic. “There’s a lot more freedom in expression now,” she said.

“You’ll see androgynous styles, statement pieces, and sustainable choices all on the same red carpet. The pressure to follow a single trend has lessened, and personal style has taken the spotlight.” It’s not just about being fashionable anymore, it’s about being authentic.

With cameras on them 24/7, celebrities today are constantly under style surveillance. “Even a run to the gym can turn into a fashion headline,” Kayal added. “Stylists are always one step ahead to make sure their clients are on-trend, but also comfortable and themselves.” Streetwear, airport looks, and paparazzi shots have become just as important as red carpet events. In fact, they’re often more talked about.

Interestingly, a lot of Y2K fashion is making its way back into wardrobes, just with a modern spin. “It’s like fashion has a short memory,” Kayal said. “Cargo pants, platform sandals, and even baby tees are cool again, especially among Gen Z. But this time around, there’s more thought in how they’re styled. People are combining old-school with new-school in really creative ways.”

Kayal noted that fashion in the early 2000s was more glam and playful, whereas today’s looks are edgier and more reflective. “Now it’s about making a statement or embracing minimalism. There’s a lot more intentionality in the way people dress.” 

As she looked back, Kayal smiled. “It’s been more than 8 years since I started. I remember watching red carpet shows on TV and now I help people walk them. Watching these changes from the inside has been incredible.” Her biggest takeaway? “Pictures really do show you everything. You don’t realize how much has changed until you look back. That’s the beauty of style, it’s ever evolving.”

These throwback photos are a real reminder of just how much time has flown by and how different our favorite celebrities looked back in the day! Which of these posts gave you that warm, fuzzy, time-traveling feeling? Feeling inspired to scroll through some old celebrity Instas? Tell us your favorites in the comments below!