The Most Daring Oscars Red Carpet Fashion Risks of All Time

 Most tend to play it safe on Oscar night with delicate ball gowns and romantic trains, but not these ladies!

These are some of the most daring and bold looks we’ve seen on Hollywood’s biggest night — some are instantly iconic, some are misses that have since become iconic.

You definitely can’t hate them for trying to stand out in the sea of chiffon and pastels.

Bjork

Bjork’s now-iconic swan dress definitely made everyone stare, but everyone gave her the “What was she thinking?” look.

Angelina Jolie

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Angelina Jolie is always stunning but this was something else! She made a modern tux look good in 2014, even though this white satin pantsuit was a little outrageous.

Charlize Theron

If Charlize Theron was trying to take a bold approach, it worked! Those rosettes though…

Faith Hill

Was Faith Hill over the rainbow? We don’t know what she was thinking but it was not pleasant.