Will Ferrell was pulling classic Will Ferrell moves by stealing his date’s tiara for himself. Other than that, Will kept to the typical attire – except that he was missing his suit jacket and stuck with only the shirt and bowtie for this picture. Still, we have a feeling he didn’t let that get in the way of any fun.
His date chose to accessorize with some unique necklaces to compliment her black dress, but her best accessory that night was her beaming smile. After all, having Will Ferrell as your prom date can hardly make for a lackluster night.
Meryl Streep
Here we have one of the most legendary acting icons in Hollywood today - Meryl Streep. Fans know that Meryl doesn’t do any of her performances halfway and, years ago, she even went all out for prom! Bright-eyed and bushy-tailed, and full of youth, Meryl was glowing at her prom in 1967.
This was a good few years before Meryl's screen debut, but it was clear that she had that star quality from the start. While managing to let her natural beauty shine through, she chose a graceful dress that included arm-length gloves. Meryl is certainly sporting a '60s debutante look here, but it looks lovely on her -- and so does her date.
Brad Pitt
Brad Pitt chose an unconventional grey suit and tie for his prom back in the 80s. And underneath his almost mullet hairstyle, you can still see the makings of People Magazine’s Sexiest Man Alive. You can also be sure it was the 80s thanks to Pitt and his date's hairstyles - they state loud and proud just which decade those locks belonged to.
As for his date, she chose a white dress that, at first glance, makes this look like a wedding photo shoot. Today she must be star-struck looking back at this photo. This lucky lady was actually one of Brad's first loves and his high school sweetheart. That's a fun story to share!
Demi Lovato
Coral is a great color on Demi Lovato, and it looked even better in this strapless dress. There is a touching backstory to this photo of her and her date. Apparently, Demi went to her friend Nolan’s prom to fulfill a childhood promise she had made.
We bet neither of them expected that Demi would be the megastar she ended up becoming by the time of the prom. And here in 2010, Demi had already secured celebrity status, which may have caused a stir at the event. But she still looked like she was having a blast just attending a friend’s high school prom.
Fergie
Fergie was sporting a very glamorous vibe in her sparkly, black prom dress. The spaghetti straps cemented the 90s look, but what really set her apart were the over-the-elbow black gloves. back then, Fergie was just another high school kid who looked forward to prom as one of the most exciting nights of her life.
And while we're sure she had a great time with her friends, we bet that night pales in comparison to all the awards shows and concerts she's been a part of since. Now a household name, Fergie has definitely retained her glamorous style through the years.