Hilariously Awkward Celebrity Oscars Photos

Have you ever compared yourself to Hollywood royalty and thought, "How do they always look so gosh darn perfect?" If this sounds familiar, then wallow no longer! As it happens, even the most famous stars haven't always been so effortlessly cool. And luckily for you, we've scoured the depths of the internet to find appearances of the most glamorous stars out there. It's time to delve into the A-lister archives and reveal the red-carpet photos these stars might be wishing had never been taken. 

Angelina Jolie

When: 1986

Angelina Jolie may be Hollywood royalty today — and always a vision of perfection — but this wasn't always the case. This photo, taken in 1986, shows when Angelina was still just actor Jon Voight's shy and adorable kid. Her older brother James Haven is in the background and mom Marcheline Bertrand is just out of shot. Nothing beats a full family affair for your first red carpet!

Gwyneth Paltrow

When: 1994

Can you believe what a total baby this GOOP mastermind looked like back in 1994? Yes, we're with you — it's difficult not to want to invent time travel just to be able to go back and ask her what shade of lipstick she was wearing. Hey, maybe Paltrow has released a toxin-free version in her beauty line.

Kate Hudson

When: 2001

Just like a celebrity's first outing on the red carpet, The Academy Awards is the perfect time for a star to make their fashion mark. When Kate Hudson attended the 2001 ceremony, her dress wasn't met with much approval. In 2014, though, the actress told the Evening Standard, “I was 21 years old when I was nominated for an Oscar for Almost Famous and to have Stella McCartney dressing me for the ceremony I felt like the hippest, coolest girl in the world. I woke up the next morning and turned on the television to find out I was on every worst-dressed list. So I called Stella, and we just laughed."

Geena Davis

When: 1992

Geena Davis was nominated for Thelma & Louise in 1992, but for the Oscars ceremony she wore a dress she probably wouldn’t even have been able to drive a car in. It was a short, ruffled affair created by Ruth Meyers and Bill Hargate. Davis topped off the look with some long satin gloves and black tights. It was, if nothing else, very ’90s.